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

HRID 1869763노트

반응식

HRID 1869763 반응식
[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]

참가 물질

5

반응물 3

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 68419343N-(tert-Butylsulfinyl)-4-(trifluoromethyl)benzenemethaneimineHCID 178455850HCID 178455850, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-467f6705bbb84d81893fb8a38ea56397
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638629B2

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