Sodium borohydride → HCID 19706768, compound

HRID 726539Notes

Reaction equation

HRID 726539 reaction equation
[F:1][C:2]([F:15])([C:5]([CH2:13][CH3:14])([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:6][CH3:7])[CH:3]=[O:4].[BH4-].[Na+]>C1COCC1.C(O)C>[F:15][C:2]([F:1])([C:5]([CH2:13][CH3:14])([O:8][Si:9]([CH3:10])([CH3:12])[CH3:11])[CH2:6][CH3:7])[CH2:3][OH:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19706767HCID 19706767, compound

Product 1

HCID 19706768HCID 19706768, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred, ice-cooled solution of 2,2-difluoro-3-ethyl-3-trimethylsilyloxy-pentanal (1.45 g, 6.08 mmol) in THF (5 ml) and ethanol (15 ml) was treated with sodium borohydride (2.76 mg, 7.30 mmol). After 30 minutes the reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine, dried over MgSO4 and concentrated. Flash chromatography (50 g silica gel; 10% EtOac in petroleum ether as eluant) afforded the title compound as a colourless oil, δ 0.15 (s, 9H), 1.36 (t, 6H), 2.48 (m, 1H), 3.93 (m, 2H).

Workup

  1. customAfter 30 minutes the reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93eaf3dae7c34b798e8f531bbf78f1ea
Source dataset
uspto-grants-1998_01
Patent number
US05710142

Reaction notes

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