tert-Butyl bromoacetate → HCID 15617409、化合物

HRID 846188ノート

反応式

HRID 846188 の反応式
[Cl-].C([Al+]CC)C.Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:16]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=[O:31])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CCCCCC.O1CCCC1.[Zn].[Cu]Br>[OH:31][CH:30]([C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

参加物

8

反応物 3

HCID 79177tert-Butyl bromoacetateHCID 140975722-DodecylbenzaldehydeHCID 16686102Diethyl aluminum chloride

生成物 1

HCID 15617409HCID 15617409、化合物収率 79%

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 24593copper(I) bromide触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A solution of diethylaluminum chloride (54.7 mmol) in hexane was added to a slurry of zinc dust (74.5 mmol) and a catalytic amount of copper (I) bromide (2.5 mmol) in anhydrous tetrahydrofuran (300 ml) while stirring under argon at 20° C. The resulting mixture was then cooled to 0° C. in an ice-methanol bath. A solution of t-butyl bromoacetate (49.8 mmol) and 2-dodecylbenzaldehyde of Example 1(c) (54.7 mmol); in anhydrous tetrahydrofuran was added slowly over 60 minutes. The reaction was stirred for about 24 hours and was permitted to warm slowly to room temperature. The mixture was filtered to remove zinc, concentrated, acidified with 3N hydrochloric acid and extracted with ether. Organic extracts were dried over magnesium sulfate, filtered, and evaporated to afford crude product. This material was then flash chromatographed on silica using 8% ethyl acetate in hexane to give the desired product in 79% yield.

後処理

  1. temperatureto warm slowly to room temperature
  2. filtrationThe mixture was filtered
  3. customto remove zinc
  4. concentrationconcentrated
  5. extractionextracted with ether
  6. dry with materialOrganic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto afford crude product
  10. customflash chromatographed on silica using 8% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-e427d845f34c47b89cfbd47ce77bf078
出典データセット
uspto-grants-1992_08
特許番号
US05135938

反応ノート

読み込み中…