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Formaldehyde → (S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol

HRID 1075553
ノート
印刷プレビュー

反応式

HRID 1075553 の反応式
[C:1]([Si:5]([O:8][C@@H:9]1[C@H:18]2[C@@:13]([CH3:21])([C:14](=CC)[CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH2:10]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH2:22]=O.[Cl-].C[Al+]C.C([O:30][CH2:31][CH3:32])C>C1(C)C=CC=CC=1.CCCCCC>[C:1]([Si:5]([CH3:7])([CH3:6])[O:8][C@H:9]1[CH2:10][CH2:11][CH2:12][C@@:13]2([CH3:21])[C@H:18]1[CH2:17][CH2:16][CH:15]=[C:14]2[C@H:32]([CH3:22])[CH2:31][OH:30])([CH3:3])([CH3:4])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 16686359Dimethylalumanylium chlorideHCID 57178905(1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethyl-silane

生成物 1

HCID 21309369(S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol収率 67.5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 3.11 g (10.1 mMol) of (1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethylsilane in 125 ml of toluene are added 0.33 g (11.1 mMol) of finely powdered paraformaldehyde. The reaction mixture is cooled to 0° C. and 12.56 ml of a one molar solution of dimethylaluminumchloride in hexane are added and kept for one hour at this temperature. The reaction mixture is stirred at room temperature overnight, diluted with diethylether, washed with 1N HCl and with water, then dried over sodium sulfate and evaporated in vacuo. The residue is chromatographed over a medium pressure 250 g silica gel column with hexane/ethylacetate 9/1 to yield 2.31 g (67.5%) of pure (S)-2-[(4aR,5S,8aS)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphtalen-1-yl]-propan-1-ol as an oil.

後処理

  1. washwashed with 1N HCl and with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue is chromatographed over a medium pressure 250 g silica gel column with hexane/ethylacetate 9/1

出典と根拠

ORDレコード
ord-c9ecf53cbb604effb591475f756fba45
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

読み込み中…

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