Ethyl caprate → 1-Decanol

HRID 1588020ノート

反応式

HRID 1588020 の反応式
CC(C)[O-].[Nd+3].CC(C)[O-].CC(C)[O-].C(O[SiH](OCC)OCC)C.[C:24](OCC)(=[O:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[SiH4].[OH-].[Na+]>C1COCC1>[CH2:24]([OH:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

参加物

7

反応物 5

HCID 8048Ethyl caprateHCID 13830TriethoxysilaneHCID 14798Sodium HydroxideHCID 23953SilaneHCID 2734134Neodymium(III) isopropoxide

生成物 1

HCID 81741-Decanol収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A dry Schlenk tube under argon was charged with 48 mg (0.15 mmol) of neodymium (III) isopropoxide. Triethoxysilane (1.4 mL, 7.5 mmol) and ethyl decanoate (696 μL, 3 mmol) were added and the reaction mixture was heated to 60° C. After 7 hours exposure of the reaction mixture to air caused a flame, presumably due to SiH4 gas evolution. After 29 hours, THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 2.5 hours. The reaction was worked up as in Example 13. Purification by flash chromatography (ether:hexane=3:7) afforded 114 mg (24% yield) of pure decanol and 263 mg (44% yield) of recovered starting material (both >95% pure by 1H-NMR analysis).

後処理

  1. waitAfter 29 hours
  2. customPurification by flash chromatography (ether:hexane=3:7)

出典と根拠

ORDレコード
ord-82c2c85ec8f54371875643c5f2fbdf37
出典データセット
uspto-grants-1993_06
特許番号
US05220020

反応ノート

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