4-(Trifluoromethyl)benzaldehyde → 2-Methyl-N-{1-[4-(trifluoromethyl)phenyl]but-3-en-1-yl}propane-2-sulfinamide

HRID 1869763ノート

反応式

HRID 1869763 の反応式
[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]

参加物

5

反応物 3

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 68419343N-(tert-Butylsulfinyl)-4-(trifluoromethyl)benzenemethaneimineHCID 178455850HCID 178455850、化合物

生成物 1

HCID 579873322-Methyl-N-{1-[4-(trifluoromethyl)phenyl]but-3-en-1-yl}propane-2-sulfinamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-50 °C

実験手順

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.

後処理

  1. customThe mixture was quenched with NH4Cl
  2. additiondiluted with water
  3. extractionwas extracted with CH2Cl2
  4. customThe organic layer was separated
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give the product
  9. additionas a 3:2 mixture of diastereoisomers

出典と根拠

ORDレコード
ord-467f6705bbb84d81893fb8a38ea56397
出典データセット
uspto-grants-2009_12
特許番号
US07638629B2

反応ノート

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