Ethyl caprate → 1-Decanol

HRID 1588021Notes

Reaction equation

HRID 1588021 reaction equation
CC(C)[O-].[Dy+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].[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

6

Reactant 4

HCID 8048Ethyl caprateHCID 13830TriethoxysilaneHCID 14798Sodium HydroxideHCID 13033546Dysprosium tripropan-2-olate

Product 1

HCID 81741-DecanolYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A dry Schlenk tube under argon was charged with 51 mg (0.15 mmol) of dysprosium (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 29 hours, GLC analysis of an aliquot taken from the reaction mixture showed 23% conversion. The reaction mixture was then heated to 70° C. After an additional 3 days, THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 3 hours. The reaction was worked up as in Example 13. Purification by flash chromatography (ether:hexane=3:7) afforded 224 mg (47% yield) of decanol (>95% pure by 1H-NMR analysis) and 40 mg of recovered starting material (84% pure, 5.5% yield).

Workup

  1. temperatureThe reaction mixture was then heated to 70° C
  2. waitAfter an additional 3 days
  3. customPurification by flash chromatography (ether:hexane=3:7)

Sources & evidence

ORD record
ord-8af92c2cf0f04bc18a39ac006ab774e9
Source dataset
uspto-grants-1993_06
Patent number
US05220020

Reaction notes

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