(Dimethyl sulfide)trihydroboron → 2-(2-Chloro-5-(hydroxymethyl)phenyl)ethanol

HRID 1689391Notes

Reaction equation

HRID 1689391 reaction equation
B.CSC.[C:5]([CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:12](O)=[O:13])(O)=[O:6]>C1COCC1>[Cl:18][C:17]1[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[CH2:8][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 579893203-(Carboxymethyl)-4-chlorobenzoic acid

Product 1

HCID 579893372-(2-Chloro-5-(hydroxymethyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane-methyl sulfide complex (2M in THF, 12.0 mL) was added portionwise over 3 minutes to a suspension of 3-(carboxymethyl)-4-chlorobenzoic acid (example 75, step a) (2.06 g) in dry THF (30 mL) at room temperature. The resulting effervescing dense suspension was stirred at room temperature for 1 hour, then heated to reflux for 1 hour. The cooled mixture was quenched by the portionwise addition of methanol (10 mL) over 2 minutes. The solution was stirred at room temperature for 30 minutes and then concentrated onto silica and purified by flash chromatography on silica eluted with 5% methanol in dichloromethane to afford the subtitled compound as a white solid. Yield 0.983 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customThe cooled mixture was quenched by the portionwise addition of methanol (10 mL) over 2 minutes
  4. stirringThe solution was stirred at room temperature for 30 minutes
  5. concentrationconcentrated onto silica
  6. custompurified by flash chromatography on silica
  7. washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-d410af46187143779e7d410944d5774b
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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