(Dimethyl sulfide)trihydroboron → 2-(2-Chloro-3-(hydroxymethyl)phenyl)ethanol

HRID 471184Notes

Reaction equation

HRID 471184 reaction equation
B.CSC.[C:5]([CH2:8][C:9]1[C:10]([Cl:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])(O)=[O:6]>C1COCC1>[Cl:18][C:10]1[C:11]([CH2:12][OH:13])=[CH:15][CH:16]=[CH:17][C:9]=1[CH2:8][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 579889673-(Carboxymethyl)-2-chlorobenzoic acid

Product 1

HCID 579892482-(2-Chloro-3-(hydroxymethyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane-methyl sulfide complex (2M in THF, 20 mL) was added portionwise over 5 minutes to a suspension of 3-(carboxymethyl)-2-chlorobenzoic acid (example 80, step b) (4.11 g) in dry THF (100 mL) at room temperature. The resulting effervescing suspension was stirred at room temperature for 30 minutes, then heated to reflux for 60 minutes, and allowed to cool to room temperature overnight. The mixture was quenched by the portionwise addition of methanol (15 mL) over 15 minutes. The mixture was diluted further with methanol to give a solution, which was then concentrated in vacuo to give a syrup. The syrup was purified by flash chromatography on silica eluted with 2% methanol in dichloromethane to the afford the crude subtitled compound as a white solid. Yield 1.44 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 60 minutes
  3. temperatureto cool to room temperature overnight
  4. customThe mixture was quenched by the portionwise addition of methanol (15 mL) over 15 minutes
  5. additionThe mixture was diluted further with methanol
  6. customto give a solution, which
  7. concentrationwas then concentrated in vacuo
  8. customto give a syrup
  9. customThe syrup was purified by flash chromatography on silica
  10. washeluted with 2% methanol in dichloromethane to the

Sources & evidence

ORD record
ord-18378592b1a34f529405b56eb595f303
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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