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

HRID 471128Notes

Reaction equation

HRID 471128 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-e16b97132ca948b8b45a6c928760a759
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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