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

HRID 6717

反応式

HRID 6717 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-789a855a27f04393a01aa7155bdee404
出典データセット
uspto-grants-2006_08
特許番号
US07084154B2

関連ノート

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