Benzenesulfonyl chloride → HCID 18790043, compound

HRID 1107138Notes

Reaction equation

HRID 1107138 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][CH:12]([CH:16]([OH:27])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]([OH:15])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(S(Cl)(=O)=O)C=CC=CC=1>N1C=CC=CC=1>[C:1]1([S:7]([CH2:10][CH2:11][CH:12]2[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:27][C:13]2=[O:15])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 18790098HCID 18790098, compound

Product 1

HCID 18790043HCID 18790043, compoundYield 112.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution containing (-)-2-(2-benzenesulfonylethyl)-3-hydroxy-7-phenylheptanoic acid (1 g, 2.56 mmol) in anhydrous pyridine (17 mL) under nitrogen atmosphere at 0° C. is added freshly distilled benzenesulfonyl chloride (0.89 g, 5.13 mmol) via syringe. The resulting dark yellow/orange-colored solution is cooled to -20° C. After 16 hours, the mixture is partitioned between ice/water (100 mL) and ethyl acetate (50 mL) and the layers are separated. The aqueous phase is extracted with ethyl acetate (2×50 mL) and the combined organic extracts are washed successively with water (4×50 mL), brine (50 mL), dried over anhydrous MgSO4, filtered and concentrated to afford a yellow oil. The crude product is combined with the product of an identical reaction performed on 1.55 g-scale and chromatographed on silica gel (pet-ether/EtOAc, 4:1) to afford (-)-3-(2-benzenesulfonyl-ethyl)-4-(4-phenylbutyl)-oxetan-2-one (1.07 g, 44%) as a pale yellow oil. TLC analysis [pet-ether/EtOAc, 2:1, Rf (acid)=0.05, Rf (lactone)=0.65]. [α]23D -10.1° (c 1.0, CHCl3); 1H NMR (300 MHz, CDCl3) δ 1.36-1.80 (m, 6H), 2.16 (m, 2H), 2.62 (t, J=7.5 Hz, 2H), 3.16 (m, 1H), 3.35 (m, 1H), 3.79 (m, 1H), 4.56 (m, 1H), 7.16 (m, 3H), 7.28 (m, 2H), 7.69 (m, 2H), 7.79 (m, 1H), 7.91 (m, 2H) ppm. Mass spectrum (EI) m/z 373 (M+H)+.

Workup

  1. customthe mixture is partitioned between ice/water (100 mL) and ethyl acetate (50 mL)
  2. customthe layers are separated
  3. extractionThe aqueous phase is extracted with ethyl acetate (2×50 mL)
  4. washthe combined organic extracts are washed successively with water (4×50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil
  9. customchromatographed on silica gel (pet-ether/EtOAc, 4:1)

Sources & evidence

ORD record
ord-06292ff5655d4ac1b458a0b4745a7b91
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

Loading…