3-Acetyl-2-methyl-5-phenylthiophene → HCID 57594999, compound

HRID 1785238Notes

Reaction equation

HRID 1785238 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7](=[O:9])[CH3:8].[Li+].[BH4-]>C1COCC1>[CH3:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[CH:7]([OH:9])[CH3:8]

Participants

4

Reactant 2

HCID 27287653-Acetyl-2-methyl-5-phenylthiopheneHCID 4148881Lithium borohydride

Product 1

HCID 57594999HCID 57594999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-Methyl-5-phenyl-thiophen-3-yl)-ethanone (1.08 g, 5.0.0 mmole) in THF (20 mL), is added to LiBH4 (0.327 g, 15.0 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 30 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 (3×50 mL). The combined organic solution is dried over Na2SO4 and concentrated to provide the titled compound as white 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 (3×50 mL)
  5. dry with materialThe combined organic solution is dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6f89c9e01fc4555ad8b0887273f9788
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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