4-(Trifluoromethyl)benzaldehyde → 2-Methyl-N-{1-[4-(trifluoromethyl)phenyl]but-3-en-1-yl}propane-2-sulfinamide
Reaction equation
[CH3:1][C:2]([S:5]([N:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6])([CH3:4])[CH3:3].F[C:20](F)(F)[C:21]1C=CC(C=O)=C[CH:22]=1.C([Mg]Br)C=C>C(Cl)Cl>[CH3:4][C:2]([S:5]([NH:7][CH:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)[CH2:22][CH:21]=[CH2:20])=[O:6])([CH3:1])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
2-Methyl-N-{[4-(trifluoromethyl)phenyl]methylene}propane-2-sulfinamide (prepared according to the procedure described in Example 99 step 1, using 4-(trifluoromethyl)benzaldehyde) (5 g, 0.18 mol) was dissolved in CH2Cl2 and the solution cooled to −50° C. Allylmagnesium bromide (10.8 mL, 2M in THF, 0.22 mol) was added dropwise and the resulting solution was stirred at 0° C. for 30 min. The mixture was quenched with NH4Cl and diluted with water and was extracted with CH2Cl2. The organic layer was separated and was washed with brine, then dried (MgSO4) and concentrated in vacuo to give the product as a 3:2 mixture of diastereoisomers.
Workup
- customThe mixture was quenched with NH4Cl
- additiondiluted with water
- extractionwas extracted with CH2Cl2
- customThe organic layer was separated
- washwas washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give the product
- additionas a 3:2 mixture of diastereoisomers
Sources & evidence
- ORD record
- ord-467f6705bbb84d81893fb8a38ea56397
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638629B2
Reaction notes
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