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

HRID 1255241Notes

Reaction equation

HRID 1255241 reaction equation
CSC.B.[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 acid2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane dimethyl sulfide complex (2M in THF, 6.50 mL) was added portionwise over 5 minutes to a solution of 5-(carboxymethyl)-2-chlorobenzoic acid [Aromatic Intermediate 7, step b] (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-599917363307422cb1acf708825766e4
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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