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<A NAME="RY02502ST-5">5</A>
Typical procedure for (±)-2-hydroxy-2-(p-ethylphenyl)-3-chlorooctanoate(3f): To a stirred solution of aluminium chloride (430 mg, 3 mmol) in CH2Cl2 (4 mL) was added the solution of methyl 2-chloro-2,3-epoxyoctanoate (206 mg, 1 mmol)
and ethylbenzene (319 mg, 3 mmol) in CH2Cl2 (2 mL) at room temperature. The mixture was stirred for 50 minutes, then reaction
was stopped by pouring the ice (10 mL), and the aqueous layer was extracted with EtOAc.
The combined extract was washed with saturated NaHCO3 solution and brine, then dried over MgSO4. Removal of the solvent gave 232 mg of a clean oil, which was purified by column
chromatography (hexane-ether = 160:1) to give 161 mg (51.5%) of (S,S)-(±)-3f and 38 mg (12.1%) of (S,R)-(±)-3f.
(S,S)-(±)-3f: yellow liquid, Rf = 0.30 (hexane-ether = 2:1); 1H NMR (200 MHz, CDCl3) δ 0.83 (t, J = 6.4 Hz, 3 H), 1.24 (t, J = 7.6 Hz, 3 H), 1.18-1.76 (m, 8 H), 2.66 (q, J = 7.6 Hz, 2 H), 3.82 (s, 3 H), 3.91 (s, 1 H), 4.68 (dd, J = 1.8 Hz and 10.8 Hz, 1 H), 7.21 (d, J = 8.4 Hz, 2 H), 7.57 (d, J = 8.4 Hz, 2 H); 13C NMR (200 MHz, CDCl3) δ 13.89, 15.28, 22.38, 26.58, 28.37, 30.51, 30.87, 53.53, 68.30, 81.23, 125.85,
127.98, 134.97, 144.34, 173.58; IR(neat): 3514, 2958, 2932, 2864, 1742, 1512, 1437,
1257, 1147, 756 cm-1; Anal. Calcd for C17H25ClO3: C, 65.27; H, 8.05; Found: C, 65.51; H, 8.22. (S,R)-(±)-3f: yellow liquid, Rf = 0.23 (hexane-ether = 2.1); 1H NMR(200 MHz, CDCl3) δ 0.90 (t, J = 6.4 Hz, 3 H), 1.24 (t, J = 7.6 Hz, 3 H), 1.20-2.10 (m, 8 H), 2.66 (q, J = 7.6 Hz, 2 H), 3.73 (s, 1 H), 3.81 (s, 3 H), 4.61 (dd, J = 1.6 Hz and 10.8 Hz, 1 H), 7.21 (d, J = 8.4 Hz, 2 H), 7.53 (d, J = 8.4 Hz, 2 H); 13C NMR (200 MHz, CDCl3) δ13.97, 15.22, 22.42, 26.57, 28.37, 31.05, 33.11, 53.58, 67.65, 81.25, 125.70, 127.83,
136.63, 144.32, 173.10; IR(neat): 3512, 2962, 2934, 2864, 1734, 1514, 1458, 1253,
1143, 835, 665 cm-1; Anal. Calcd for C17H25ClO3: C, 65.27; H, 8.05; Found: C, 65.51; H, 8.22.
<A NAME="RY02502ST-6">6</A>
X-ray crystallographic data of syn-3d: data collection, solution, and refinement.
Chemical formula: C14H19O3Cl; F. W. = 270.76; crystal size: 0.50 × 0.25 × 0.43 mm3; crystal system: triclinic; lattice parameters: a = 10.495(3), b = 11.755(3), c = 6.608(2) Å, α = 100.36(2), β = 107.25(3), γ = 69.213(18)º, V = 725.4(4) Å3; space group: P (#2); Z = 2; Dcalc = 1.240 g/cm3; F(000) = 288; µ(Mo Kα) = 0.26 mm-1; diffractometer: Rigku AFC5R; T: 25 ºC; no. of reflections measured: total 3880, unique 3334; structure solution:
direct methods (SIR92); refinement: full-matrix least-squares on F
2; function mini-mized: Σw (Fo2 - Fc2)2; least squares weights: 1/σ2(Fo) = 4Fo2/σ2 (Fo2); no. obsd [I > 0.5σ (I)]: 2886; no. variables: 240; residuals R
1, wR
2: 0.063, 0.099; goodness of fit indicator: 1.94;
max /ρmin: 0.23 / - 0.28 e / Å3.