Acetyl chloride → HCID 10945913, compound

HRID 2307527Notes

Reaction equation

HRID 2307527 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[S:15][CH2:14][C@H:13]([OH:16])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=[O:19])[CH3:18].C(=O)(O)[O-].[Na+]>ClCCl.N1C=CC=CC=1>[C:1]([O:9][CH2:10][C@H:11]1[S:15][CH2:14][C@H:13]([O:16][C:17](=[O:19])[CH3:18])[O:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 69435312HCID 69435312, compound

Product 1

HCID 10945913HCID 10945913, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 29.76 g (0.132 mol) of cis and trans 2-benzoyloxymethyl-5-hydroxy-1,3-oxathiolane (as prepared in Example 1) in dichloromethane (65 mL) and pyridine (32 mL) was added dropwise 28.1 mL (0.395 mol) of acetyl chloride at 0-5° C. over 1.5 to 2 hours. The reaction mixture was stirred at 0-5° C. for 30 minutes then it was poured carefully onto a cold (0° C.) solution of saturated sodium bicarbonate. The organic layer was separated and the water layer was extracted with dichloromethane (3×20 mL). The combined organic layers were washed with saturated sodium bicarbonate (3×20 mL) and brine (20 mL), and was dried over sodium sulfate. Following filtration, the solvents were removed in vacuo to give 32.1 g of crude product which was purified by Kugelrohr distillation or filtration through a short silica gel column (eluent hexanes: EtOAc 3:1). The purified product consisted of a 3:1 mixture of trans:cis isomers.

Workup

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with dichloromethane (3×20 mL)
  3. washThe combined organic layers were washed with saturated sodium bicarbonate (3×20 mL) and brine (20 mL)
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltration
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-6cc9dd44ca2d49d3b0625f43c98da956
Source dataset
uspto-grants-2004_12
Patent number
US06831174B2

Reaction notes

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