Sodium borohydride → 1-(5,6-Dichloro-pyridin-3-yl)-ethanol

HRID 2369449Notes

Reaction equation

HRID 2369449 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[O:13])[CH3:12])[CH:7]=[N:8][C:9]=1[Cl:10]>CO>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([OH:13])[CH3:12])[CH:7]=[N:8][C:9]=1[Cl:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 101980061-(5,6-Dichloropyridin-3-yl)ethan-1-one

Product 1

HCID 115935821-(5,6-Dichloro-pyridin-3-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a well stirred suspension of sodium borohydride (66.21 g, 1.75 mole) in methanol (3.5 L) cooled to 0° C. with a dry ice/acetone bath was added 1-(5,6-dichloro-pyridin-3-yl)-ethanone 8 (665 g, 3.5 mole) at a rate such that the temperature remained at 0° C. After solid addition was complete, the reaction mixture was stirred an additional 1 h, after which time LC/MS analysis of an aliquot showed that the reaction was complete.

Workup

  1. customremained at 0° C
  2. additionAfter solid addition
  3. stirringthe reaction mixture was stirred an additional 1 h

Sources & evidence

ORD record
ord-49a8ec7888db4b248111edf03b5f45ff
Source dataset
uspto-grants-2014_04
Patent number
US08703962B2

Reaction notes

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