Benzenesulfonyl chloride → HCID 10680344, compound

HRID 1107146Notes

Reaction equation

HRID 1107146 reaction equation
O[C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@H:3]([CH3:7])[C:4]([OH:6])=[O:5].C1(S(Cl)(=O)=O)C=CC=CC=1>N1C=CC=CC=1>[CH3:7][C@H:3]1[C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:5][C:4]1=[O:6]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 57001717HCID 57001717, compound

Product 1

HCID 10680344HCID 10680344, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (-)-(2S,3S)-3-hydroxy-2-methyl-7-phenylheptanoic acid (0.79 g, 3.3 mmol) in pyridine (30 mL) is cooled to 0° C. and benzenesulfonyl chloride (0.85 mL, 6.7 mmol) is added over 1 minute. The reaction is stirred in ice for 5 minutes, at room temperature for 2 hours and then at 0° C. for 16 hours. The reaction is poured into ice (40 mL) and extracted with ether (100 mL). The organic phase is washed with NaHCO3 (30 mL), 1N HCl (2×20 mL) and water (2×30 mL). The organic phase is dried over MgSO4 and concentrated in vacuo. The crude product is purified by column chromatography (silica, 25% ether in petroleum ether) to give (3S,4S)-3-Methyl-4-(4-phenylbutyl)oxetan-2-one (0.28 g, 39%): 1H NMR (300 MHz, CDCl3) δ 7.31-7.21 (m, 2H), 7.19-7.15 (m, 3H), 4.19-4.13 (m, 1H), 3.25-3.16 (m, 1H), 2.64 (t, J=7.6 Hz, 2H), 1.95-1.64 (m, 4H), 1.55-1.40 (m, 2H), 1.36 (d, J=7.8 Hz, 3H); MS (EI) m/e 218 (M+).

Workup

  1. waitat 0° C. for 16 hours
  2. extractionextracted with ether (100 mL)
  3. washThe organic phase is washed with NaHCO3 (30 mL), 1N HCl (2×20 mL) and water (2×30 mL)
  4. dry with materialThe organic phase is dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (silica, 25% ether in petroleum ether)

Sources & evidence

ORD record
ord-be2d076cc3a64bd4943f508d618765be
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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