Tetrahydrofuran → Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

HRID 846189노트

반응식

HRID 846189 반응식
[Cl-].C([Al+][CH2:5][CH3:6])C.Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:16]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34](SC1N(CCCC(O)=O)N=NN=1)C(O)=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[O:50]1CCCC1>CCCCCC.[Zn].[Cu]Br>[OH:50][CH:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:6][CH:5]=1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

참가 물질

8

반응물 4

HCID 8028Tetrahydrofuran2회HCID 79177tert-Butyl bromoacetateHCID 16686102Diethyl aluminum chlorideHCID 198803822-(2-Dodecylphenyl)-2-[[1-(3-carboxypropyl)-5-tetrazolyl]thio]acetic acid

생성물 1

HCID 15617420Tert-butyl 3-hydroxy-3-[2-(8-phenyloctyl)phenyl]propionate

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 24593copper(I) bromide촉매HCID 8058Hexane용매

반응 조건

온도
-20 °C

실험 절차

A solution of diethlaluminum chloride (0.0082 moles, 8.2 ml) in hexane was added to a slurry of zinc dust (0.0111 mol: 0.7248 g) and a catalytic amount of copper (I) bromide (0.004 mol; 0.0585 g) in anhydrous tetrahydrofuran (40 ml) while stirring under argon at 20° C. the resulting mixture was then cooled to -20° C. in an ice-methanol bath. A solution of t-butyl bromoacetate (0.0082 mol; 1.32 ml) and 2-(8-phenyloctyl)benzylaldehyde of Example 5(a) or (b) (0.0082 moles; 2.3969 g) in anhydrous tetrahydrofuran was added slowly over 60 min. The reaction was stirred overnight and was permitted to warm up slowly to room temperature. The mixture was filtered to remove zinc, concentrated, and azeotroped with methylene chloride. The resulting oil was then chromatographed on silica using 5% ethyl acetate in hexane with 0.5% formic acid to yield the desired product.

후처리

  1. temperatureto warm up slowly to room temperature
  2. filtrationThe mixture was filtered
  3. customto remove zinc
  4. concentrationconcentrated
  5. customazeotroped with methylene chloride
  6. customThe resulting oil was then chromatographed on silica using 5% ethyl acetate in hexane with 0.5% formic acid

출처 및 근거

ORD 기록
ord-6f16b235f1344b378bd1cdc68173c15c
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05135938

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