Ethyl caprate → 1-Decanol

HRID 1588020Notes

Reaction equation

HRID 1588020 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

HCID 81741-DecanolYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-82c2c85ec8f54371875643c5f2fbdf37
Source dataset
uspto-grants-1993_06
Patent number
US05220020

Reaction notes

Loading…