Sodium borohydride → HCID 57594981, compound

HRID 1785228Notes

Reaction equation

HRID 1785228 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[S:4][C:3]=1[CH:17]([CH3:20])[CH:18]=[O:19].[BH4-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=2)[S:4][C:3]=1[CH:17]([CH3:20])[CH2:18][OH:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57594990HCID 57594990, compound

Product 1

HCID 57594981HCID 57594981, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-propionaldehyde (1.40 g, 4.69 mmole) in THF (20 mL), is added to NaBH4 (0.266 g, 7.04 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using NH4Cl(aq) (50 mL) at 0° C. The THF is removed on rota vapor, the aqueous solution is then extracted with ethyl acetate (2×50 mL). The combined organic solution is washed with brine (3×100 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, gradient eluting with 0-20% ethyl acetate in hexane and concentrated to provide the titled compound as white solid.

Workup

  1. customThe reaction is quenched
  2. customat 0° C
  3. customThe THF is removed on rota vapor
  4. extractionthe aqueous solution is then extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic solution is washed with brine (3×100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is purified on a silica gel column
  9. washgradient eluting with 0-20% ethyl acetate in hexane
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a1f6a4333a694a84bfcc046a232e3074
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

Loading…