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

HRID 846189ノート

反応式

HRID 846189 の反応式
[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]

参加物

8

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 79177tert-Butyl bromoacetateHCID 16686102Diethyl aluminum chlorideHCID 198803822-(2-Dodecylphenyl)-2-[[1-(3-carboxypropyl)-5-tetrazolyl]thio]acetic acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 24593copper(I) bromide触媒HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f16b235f1344b378bd1cdc68173c15c
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…