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Sodium hydride → 2-(7-Hydroxyheptyl)-3-(4-methyl-3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

HRID 442448
ノート
印刷プレビュー

反応式

HRID 442448 の反応式
[CH3:1][CH:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C:3](=[O:11])[CH2:4]P(=O)(OC)OC.[H-].[Na+].[H][H].[CH:20]([CH:22]1[CH2:26][CH:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:24]([OH:34])[CH:23]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][OH:42])=O>O1CCCC1.C(O)(=O)C>[OH:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH:23]1[CH:22]([CH:20]=[CH:4][C:3](=[O:11])[CH:2]([CH3:1])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:26][CH:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:24]1[OH:34]
参加物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 24758Sodium hydrideHCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonateHCID 203548513-Formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 867350452-(7-Hydroxyheptyl)-3-(4-methyl-3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol収率 93.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of dimethyl 3-methyl-2-oxoheptylphosphonate (2.36 g.) in tetrahydrofuran (20 ml.) was added dropwise to a stirred suspension of sodium hydride (0.24 g.) in tetrahydrofuran (50 ml.). The mixture was stirred at room temperature until the evolution of hydrogen has ceased, then treated dropwise with a solution of 3-formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanol [3.28 g.; prepared as described above in Example 2(e)] in tetrahydrofuran (20 ml.) and stirred for a further 2 hours. The mixture was acidified to pH 4 by the addition of glacial acetic acid, the solvent was removed in vacuo and the residue dissolved in diethyl ether. The ethereal solution was washed with aqueous sodium carbonate solution, dried over magnesium sulphate, and evaporated to dryness to give 2-(7-hydroxyheptyl)-3-(4-methyl-3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol (4.1 g.).

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in diethyl ether
  3. washThe ethereal solution was washed with aqueous sodium carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-d20a619bcf564cc3bb8e5ccc4b3c392f
出典データセット
uspto-grants-1977_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04045467

反応ノート

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