Ammonium Chloride → Cyclohexyl{2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methanol

HRID 1876990Notes

Reaction equation

HRID 1876990 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2].[CH:20]1([Mg]Br)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:20]1([CH:8]([C:7]2[CH:6]=[C:5]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=3)[S:4][C:3]=2[CH2:1][CH3:2])[OH:9])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866463692-Ethyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehydeHCID 178420632HCID 178420632, compound

Product 1

HCID 68511801Cyclohexyl{2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-5-[4-(trifluoromethyl)phenyl]thiophene-3-carbaldehyde (2.00 g) synthesized above in tetrahydrofuran (40 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (14.1 mL) at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane to ethyl acetate:hexane=1:4, volume ratio) to give the title compound (2.29 g, 88%) as a yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane to ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-f47ca9aa6a4e410da4189c1ec71fb8ae
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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