Sodium borohydride → [3-Methyl-4'-(trifluoromethyl)biphenyl-4-yl]methanol

HRID 1669228Notes

Reaction equation

HRID 1669228 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][C:6]=1[CH3:21])=O.[BH4-].[Na+].CCOC(C)=O.CCCCCC>C1COCC1.CO>[CH3:21][C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[CH:9]=[CH:10][C:5]=1[CH2:3][OH:2]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 673420563-Methyl-4'-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 22280004[3-Methyl-4'-(trifluoromethyl)biphenyl-4-yl]methanolYield 99%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester (300 mg, 1.02 mmol) in THF/MeOH (10/3 mL) is added portion-wise sodium borohydride (386 mg, 10.20 mmol) and heated to reflux. After 1 h TLC (20% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture is concentrated and the residue is partitioned between EtOAc (100 mL) and 0.2N HCl (20 mL). The aqueous layer is extracted with a second portion of EtOAc (50 mL). The combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated to yield the title compound (268 mg, 99%). 1NMR (400 MHz, CDCl3) δ ppm: 7.69 (s, 4H), 7.50-7.39 (m, 3H), 4.77 (s, 2H), 2.44 (s, 3H).

Workup

  1. temperatureheated to reflux
  2. customconsumption of starting material
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is partitioned between EtOAc (100 mL) and 0.2N HCl (20 mL)
  5. extractionThe aqueous layer is extracted with a second portion of EtOAc (50 mL)
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5ff0d6cbfca749efb87e11121123c2f1
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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