Sodium borohydride → 2-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-

HRID 2235646Notes

Reaction equation

HRID 2235646 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO.C1COCC1>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]([CH2:14][OH:15])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 46748195-(4-(Trifluoromethyl)phenyl)thiophene-2-carbaldehyde

Product 1

HCID 219863522-Thiophenemethanol, 5-[4-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 61.2 (0.87 g, 3.40 mmol) in 3:2 MeOH/THF (25 mL) was added NaBH4 (0.13 g, 3.40 mmol) as a solid in one portion. The mixture was stirred for 2 hours at room temperature and concentrated. The residue was suspended in 1N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to afford 61.3 as a white powder. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.68 (d, 2H), 7.62 (d, 2H), 7.26 (d, 1H), 7.01 (d, 1H), 4.86 (d, 2H), 1.84 (t, 1H).

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0948a0482211428d8ea87b76b8db2188
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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