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Isobutyraldehyde → (1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethyl-silane

HRID 1075552
ノート
印刷プレビュー

反応式

HRID 1075552 の反応式
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH2:11][C:12]2=O)([CH3:4])([CH3:3])[CH3:2].[CH:21](=O)[CH:22](C)C>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1.C(OCC)C>[C:1]([Si:5]([O:6][C@@H:7]1[C@H:8]2[C@@:13]([CH3:17])([C:12](=[CH:21][CH3:22])[CH2:11][CH2:10][CH2:9]2)[CH2:14][CH2:15][CH2:16]1)([CH3:20])[CH3:19])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6561IsobutyraldehydeHCID 21309364(4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one

生成物 1

HCID 57178905(1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethyl-silane収率 95%

試薬・触媒・溶媒 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒2 回
HCID 3283
Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A suspension of 11.8 g (31.7 mMol) of ethyltriphenylphosphoniumbromide in 64 ml of tetrahydrofuran is treated under stirring and argon atmosphere with 31.9 ml of a one molar solution of potassiumtertiobutylate and the resulting orange suspension treated with a solution of 3.17 g (10.7 mMol) of (4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-naphtalen-1-one in 64 ml of tetrahydrofuran and kept at room temperature for 3 hours. An additional 11.8 g (31.7 mMol) of ethyltriphenylphosphoniumbromid and 31.9 ml of a one molar solution of potassiumtertiobutylate in tetrahydrofurane are added and the reaction mixture kept overnight. Isobutyraldehyde (5.4 ml) is added, the reaction is stirred for 10 minutes, diluted with diethylether and filtered over Florisil using diethylether as eluent. After evaporation in vacuo, the residue (4.79 g) is chromatographed over 120 g of silica gel with hexane to yield 3.15 g (95%) of pure (1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethyl-silane (E/Z 4/1) as an oil.

後処理

  1. additionis treated
  2. waitthe reaction mixture kept overnight
  3. stirringthe reaction is stirred for 10 minutes
  4. filtrationfiltered over Florisil
  5. customAfter evaporation in vacuo
  6. customthe residue (4.79 g) is chromatographed over 120 g of silica gel with hexane

出典と根拠

ORDレコード
ord-50326dabcc4e4cbc885572aee04756d7
出典データセット
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05905074

反応ノート

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