4-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid → (4-Phenyl-5-(trifluoromethyl)thiophen-2-yl)methanol

HRID 1454332Notes

Reaction equation

HRID 1454332 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16](O)=[O:17])[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[OH:17][CH2:16][C:9]1[S:10][C:11]([C:12]([F:15])([F:13])[F:14])=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1

Participants

3

Reactant 1

HCID 27833724-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid

Product 1

HCID 2781490(4-Phenyl-5-(trifluoromethyl)thiophen-2-yl)methanolYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.10 g (7.7 mmol) of 4-phenyl-5-trifluoromethyl-thiophene-2-carboxylic acid (from Aldehyde 15, Step C) in 20 mL of THF was treated with 5.0 mL of 2.0 M borane dimethylsulfide complex in THF. The resulting solution was heated at reflux for 3 h, cooled to rt, quenched with 10 mL of MeOH and concentrated. Chromatography on a Biotage 40M cartridge using 9:1 v/v hexanes/EtOAc as the eluant afforded 1.95 g (98%) of the title compound: 1H NMR (500 Mhz) δ 2.05 (app s, 1H), 4.87 (s, 2H), 6.99 (s, 1H), 7.41 (app s, 5H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 3 h
  3. customquenched with 10 mL of MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fadd143da4ef474bbc179d1587243e31
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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