Sodium borohydride → HCID 59729431, compound

HRID 1669231Notes

Reaction equation

HRID 1669231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]=[O:10].[BH4-].[Na+].CCOC(C)=O.CCCCCC>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][OH:10]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 59729402HCID 59729402, compound

Product 1

HCID 59729431HCID 59729431, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a 0° C. solution of (3-fluoro-4′-trifluoromethyl-biphenyl-4-yl)-acetaldehyde (372 mg, 1.31 mmol) in THF/MeOH (10/3 mL) is added portion-wise sodium borohydride (100 mg, 2.62 mmol) and warmed to room temperature. After 1 h TLC (30% 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 (374 mg, quant.). 1NMR (400 MHz, CDCl3) δ ppm: 7.68 (q, 4H, J=8.2 Hz), 7.38-7.32 (m, 2H), 7.29 (d, 1H, J=11.0 Hz), 3.92 (t, 2H, J=6.6 Hz), 2.97 (t, 2H, J=6.6 Hz).

Workup

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

Sources & evidence

ORD record
ord-62e009aa590e4a5f864cb489178d023e
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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