Ethyl caprate → 1-Decanol

HRID 1588020노트

반응식

HRID 1588020 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

HCID 81741-Decanol수율 24%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-82c2c85ec8f54371875643c5f2fbdf37
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05220020

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