Sodium borohydride → 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol

HRID 875255Notes

Reaction equation

HRID 875255 reaction equation
[Cl:1][CH2:2][C:3]([CH:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[O:6]1)=[O:4].[BH4-].[Na+]>C(O)C.O.ClCCl>[Cl:1][CH2:2][CH:3]([CH:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:7]=2[O:6]1)[OH:4]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 866579942-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone

Product 1

HCID 672125072-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanolYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanone (0.33 g, 1.28 mmol, 88.4% A) in ethanol (2.5 ml) was cooled to 0° C. under nitrogen. NaBH4 (60.1 mg, 1.59 mmol) was added to the solution and the reaction mixture stirred for 2 hours. After checking by GPC that the starting product had disappeared, the mixture was diluted with demineralized water (7 ml) and dichloromethane (7 ml) and the phases separated. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to give crude 2-Chloro-1-(6-fluoro-1-benzopyran-2-yl)-ethanol as a mixture of diastereoisomers 54:46 (0.30 g, 70% yield, 67.9% A).

Workup

  1. customthe phases separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-be09a0a66b9d45849aaa9811caf8eb00
Source dataset
uspto-grants-2015_03
Patent number
US08981127B2

Reaction notes

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