Sodium borohydride → [3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-methanol

HRID 1785224Notes

Reaction equation

HRID 1785224 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:6][C:5]=1[CH:19]=[O:20])([CH3:3])=[CH2:2].[BH4-].[Na+]>C1COCC1>[C:1]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:11][CH:10]=2)[S:6][C:5]=1[CH2:19][OH:20])([CH3:3])=[CH2:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86604774HCID 86604774, compound

Product 1

HCID 68853480[3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.084 g, 0.283 mmole) in THF (3 mL), is added to NaBH4 (0.023 g, 0.622 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 saturated NH4Cl(aq) (20 mL) at 0° C. The THF is removed on rota vapor, the aqueous solution is then extracted with ethyl acetate (2×10 mL). The combined organic solution is washed with brine (3×20 mL), dried over Na2SO4 and concentrated to provide the titled compound as yellow solid, which is used for the next step without further purification.

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 (2×10 mL)
  5. washThe combined organic solution is washed with brine (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e70bee66491d4194abaaf67ed0f9b594
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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