Diethyl Ether → 1-{3-Methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanol

HRID 1785230

Reaction equation

HRID 1785230 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]=[O:18].C[Mg+].[Br-].[CH2:22](OCC)C>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]([OH:18])[CH3:22]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 219865503-Methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 219863591-{3-Methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.130 g, 0.481 mmole) in THF (5 mL), is injected 3.0 M MeMgBr in ethyl ether (0.27 mL, 0.810 mmole) dropwise. The reaction is stirred for 2 hours. The reaction is quenched with saturated NH4Cl(aq) (10 mL), then the aqueous solution is extracted with ethyl acetate (3×15 mL). The combined organic solution is washed with brine (3×50 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 0-20% ethyl acetate in hexane and concentrated to provide the titled compound as yellow solid.

Workup

  1. customThe reaction is quenched with saturated NH4Cl(aq) (10 mL)
  2. extractionthe aqueous solution is extracted with ethyl acetate (3×15 mL)
  3. washThe combined organic solution is washed with brine (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product is purified on a silica gel column
  7. washeluting with 0-20% ethyl acetate in hexane
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c3090dad9ce47efa1756af0259d6d3c
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Linked notes

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