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

HRID 1785217

Reaction equation

HRID 1785217 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.[Li+].[BH4-]>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 4148881Lithium borohydrideHCID 46748195-(4-(Trifluoromethyl)phenyl)thiophene-2-carbaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (3.02 g, 11.8 mmole) in THF (100 mL), is added to LiBH4 (1.75 g, 80.24 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 1 hour. The reaction is quenched using 5N HCl (100 mL) at 0° C. The THF is removed on rota vapor, the aqueous solution is then extracted with ethyl acetate (2×100 mL). The combined organic solution is washed with brine (3×200 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 20% ethyl acetate in hexane and concentrated to provide the titled compound as off-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 (2×100 mL)
  5. washThe combined organic solution is washed with brine (3×200 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is purified on a silica gel column
  9. washeluting with 20% ethyl acetate in hexane
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b5e75adf0e48869f9a9fff941b564e
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Linked notes

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