Sodium borohydride → HCID 69946895, compound

HRID 566523Notes

Reaction equation

HRID 566523 reaction equation
[BH4-].[Na+].[C:3]([C@H:8]1[S:12][CH2:11][C@H:10]([O:13][C:14](=[O:16])[CH3:15])[O:9]1)(OCC)=[O:4].CCOC(C)=O.CCCCCC>CO>[OH:4][CH2:3][C@H:8]1[S:12][CH2:11][C@H:10]([O:13][C:14](=[O:16])[CH3:15])[O:9]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 69740094HCID 69740094, compound

Product 1

HCID 69946895HCID 69946895, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (27 mg, 0.708 mmol) was added to a magnetically stirred solution of trans-2-carboethoxy-5-acetoxy-1,3-oxathiolane (52 mg, 0.236 mmol) in methanol (1 mL) at 0° C. under an argon atmosphere. The resultant solution was stirred for 25 minutes at 0° C. The reaction was quenched with 2 drops of saturated ammonium chloride solution followed by dilution with diethyl ether (4 mL). This mixture was stirred at room temperature for 15 minutes and then was dried over anhydrous magnesium sulphate. The drying agent was removed by suction filtration and the filtrate was concentrated under reduced pressure. The crude product obtained was subjected to column chromatography (50% EtOAc-hexane) to afford 21 mg (50%) of the title compound.

Workup

  1. customThe reaction was quenched with 2 drops of saturated ammonium chloride solution
  2. dry with materialwas dried over anhydrous magnesium sulphate
  3. customThe drying agent was removed by suction filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product obtained

Sources & evidence

ORD record
ord-fb6662a38e2f4cc3bbdeb821a6635cfa
Source dataset
uspto-grants-2001_01
Patent number
US06175008B1

Reaction notes

Loading…