Benzoyl chloride → 2(S)-(benzoyloxymethyl)-1,3-oxathiolane

HRID 1689575Notes

Reaction equation

HRID 1689575 reaction equation
[OH:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[C:8]([O:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 46244897HCID 46244897, compound

Product 1

HCID 596089912(S)-(benzoyloxymethyl)-1,3-oxathiolaneYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2(S)-(Hydroxymethyl)-1,3-oxathiolane (0.25 mmol, 30 mg, 1.0 equiv.) recovered from Example 3 was treated with benzoyl chloride (0.25 mmol, 35 mg, 1.0 equiv.), triethylamine (0.25 mmol, 25 mg, 1.0 equiv.) in dichloromethane (1 mL) at ambient temperature while monitoring the reaction progress by TLC. After 1 h, the reaction was extracted with saturated ammonium chloride solution and brine. The organic phase was concentrated and chromatographed on silica gel to give 2(S)-(benzoyloxymethyl)-1,3-oxathiolane (25 mg, 44.6%).

Workup

  1. extractionthe reaction was extracted with saturated ammonium chloride solution and brine
  2. concentrationThe organic phase was concentrated
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-2b1d43f87cb148e4864d59d7e1a195a5
Source dataset
uspto-grants-2012_04
Patent number
US08153416B2

Reaction notes

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