Water → cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

HRID 6717

반응식

HRID 6717 반응식
[Br-].[C:2]1(=[O:34])[N:6]([CH2:7][CH2:8][CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:5](=[O:29])[C:4]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:3]12.[Cl:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=O.CC(C)([O-])C.[K+].O>O1CCCC1>[Cl:35][C:36]1[CH:37]=[C:38](/[CH:39]=[CH:9]\[CH2:8][CH2:7][N:6]2[C:2](=[O:34])[C:3]3=[CH:33][CH:32]=[CH:31][CH:30]=[C:4]3[C:5]2=[O:29])[CH:41]=[CH:42][CH:43]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 114773-ChlorobenzaldehydeHCID 22018487(3-(1,3-Dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 58679826cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide수율 64.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A mixture of 3-phthalimidopropyltriphenylphosphonium bromide (15.1 g) and 3-chlorobenzaldehyde (4.0 g, Aldrich, U.S.A.) in tetrahydrofuran (150 mL) was cooled to −78° C. in a dry ice/acetone bath. Potassium tert-butoxide (3.2 g) was added and the mixture was stirred for 20 min, then allowed to warm to 0° C. After four hours, the solution was poured into 200 mL water and extracted three times with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, and reduced in vacuo. The residue was dissolved in 200 mL of a 1:1 mixture of ethyl acetate/hexanes, and filtered through a short silica gel plug to remove the triphenylphosphine oxide byproduct. Evaporation of the filtrate yielded 5.7 g of cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide in a 10:1 ratio of cis:trans isomers.

후처리

  1. temperatureto warm to 0° C
  2. waitAfter four hours
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers were dried over sodium sulfate
  5. dissolutionThe residue was dissolved in 200 mL of a 1:1 mixture of ethyl acetate/hexanes
  6. filtrationfiltered through a short silica gel plug
  7. customto remove the triphenylphosphine oxide byproduct
  8. customEvaporation of the filtrate

출처 및 근거

ORD 기록
ord-789a855a27f04393a01aa7155bdee404
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

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