Methanol → 2-Chloro-1-(6-chloropyridin-2-yl)ethan-1-ol

HRID 274061Notes

Reaction equation

HRID 274061 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([CH2:10][Cl:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.B.C1(C2(C3C=CC=CC=3)OBN3CCC[C@H]23)C=CC=CC=1.CO>O1CCCC1>[Cl:11][CH2:10][CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[OH:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 6331Borane2×HCID 155504512-Chloro-1-(6-chloropyridin-2-YL)ethanoneHCID 178419123HCID 178419123, compound

Product 1

HCID 200947722-Chloro-1-(6-chloropyridin-2-yl)ethan-1-olYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of chloromethyl 6-chloro-2-pyridyl ketone (8.126 g) in tetrahydrofuran (32 ml) and a solution of borane in tetrahydrofuran (1.0M, 25.7 ml) were added simultaneously to a mixture of a solution (R)-tetrahydro-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]-oxazaborole in tetrahydrofuran (ca. 0.335M, 8.9 ml) and a solution of borane in tetrahydrofuran (1.0M, 4.3 ml) at -5° C. under nitrogen atmosphere over 0.5 hour and the whole was stirred for 3.5 hours. Methanol (10.4 ml) was added dropwise to the mixture at 0° C. and the whole was stirred at ambient temperature overnight. The mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform as an eluent to give (-)-2-chloro-1-(6-chloro-2-pyridyl)ethanol (7.98 g) as an oil.

Workup

  1. stirringthe whole was stirred at ambient temperature overnight
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel with chloroform as an eluent

Sources & evidence

ORD record
ord-f0d874c8cf7f4b5bb2914df336cbc2db
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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