tert-Butyl bromoacetate → HCID 15617409, 화합물

HRID 846188노트

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HRID 846188 반응식
[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]

참가 물질

8

반응물 3

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

생성물 1

HCID 15617409HCID 15617409, 화합물수율 79%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 24593copper(I) bromide촉매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e427d845f34c47b89cfbd47ce77bf078
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05135938

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