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

HRID 2423262Notes

Reaction equation

HRID 2423262 reaction equation
[Cl:1][CH2:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[O:4].[BH4-].[Na+]>C(O)C.O.ClCCl>[Cl:1][CH2:2][CH:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)[OH:4]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 167553872-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone

Product 1

HCID 672431242-Chloro-1-(6-fluorochroman-2-yl)ethanolYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution under stirring of 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-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 that the starting product had disappeared by GC, the mixture was diluted with demi water (7 ml) and dichloromethane (7 ml) and the phases separated. The organic stratum was dried under anhydrous sodium sulphate, filtered and concentrated under vacuum to give raw 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl) ethanol as a mixture of diastereoisomers 54:46 (0.30 g, 70% yield, 67.9 A %).

Workup

  1. customthe phases separated
  2. customThe organic stratum was dried under anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-63c947e7ab5145d2ab3af2f0f34bffe0
Source dataset
uspto-grants-2011_06
Patent number
US07960572B2

Reaction notes

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