(Dimethyl sulfide)trihydroboron → 2-(4-Chloro-3-(hydroxymethyl)phenyl)ethanol

HRID 1689357Notes

Reaction equation

HRID 1689357 reaction equation
B.CSC.[C:5]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:18])=[C:13]([CH:17]=1)[C:14](O)=[O:15])(O)=[O:6]>C1COCC1>[Cl:18][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:5][OH:6])=[CH:17][C:13]=1[CH2:14][OH:15]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 579893705-(Carboxymethyl)-2-chlorobenzoic acid

Product 1

HCID 579892912-(4-Chloro-3-(hydroxymethyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane-methyl sulfide complex (2M in THF, 6.50 mL) was added portionwise over 5 minutes to a solution of 5-(carboxymethyl)-2-chlorobenzoic acid (example 61, step a) (1.37 g) in dry THF (20 mL) at room temperature. The resulting effervescing solution was stirred at room temperature for 1.5 hours, then heated to reflux for 1 hour. The cooled mixture was quenched by the portionwise addition of methanol (5 mL) over 5 minutes. The solution was stirred at room temperature for 2 hours and then purified by flash chromatography on silica eluted with 5% methanol in dichloromethane to afford the subtitled compound as a colourless oil. Yield 0.933 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customThe cooled mixture was quenched by the portionwise addition of methanol (5 mL) over 5 minutes
  4. stirringThe solution was stirred at room temperature for 2 hours
  5. custompurified by flash chromatography on silica
  6. washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-da6f0e4f8ed74a6180b19411a5815f84
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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