Sodium borohydride → HCID 19937310, compound

HRID 36586Notes

Reaction equation

HRID 36586 reaction equation
[F:1][C:2]([F:16])([CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:3](OCC)=[O:4].[BH4-].[Na+]>C(O)C>[F:16][C:2]([F:1])([CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54421599Ethyl 2,2-difluoro-3-tetrahydropyranyloxypropionate

Product 1

HCID 19937310HCID 19937310, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of ethyl 2,2-difluoro-3-tetrahydropyranyloxypropionate (3.5 g, 15 mmol) in absolute ethanol (10 ml) was added dropwise to a slurry of sodium borohydride (0.57 g, 15 mmol) at room temperature in absolute ethanol (20 ml). Then the mixture was stirred an additional hour at room temperature. Then the mixture was concentrated in vacuo, hydrolyzed with aqueous ammonium chloride, extracted with ethyl acetate and dried over magnesium sulfate. The product was purified by flash chromatography on silica gel (ethyl acetate:hexane; 25:75) (2.7 g, 90%).

Workup

  1. concentrationThen the mixture was concentrated in vacuo, hydrolyzed with aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customThe product was purified by flash chromatography on silica gel (ethyl acetate:hexane; 25:75) (2.7 g, 90%)

Sources & evidence

ORD record
ord-b3ae0d307d1048128c7b525e9adc08a6
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Reaction notes

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