Ethyl formate → HCID 89106885, compound

HRID 1042417Notes

Reaction equation

HRID 1042417 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[C:8]([CH3:10])([CH3:9])[C:7]2[C:11]([CH2:13][CH2:14][CH2:15][C:6]=2[C:5]1([CH3:17])[CH3:16])=[O:12].[CH:18](OCC)=[O:19]>C(COC)OC>[CH3:17][C:5]1([CH3:16])[C:6]2[CH2:15][CH2:14][CH:13]([CH:18]=[O:19])[C:11](=[O:12])[C:7]=2[C:8]([CH3:9])([CH3:10])[CH:4]1[CH3:3]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 92292(+-)-Cashmeran

Product 1

HCID 89106885HCID 89106885, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A 2 L reaction flask was charged with sodium hydride (NaH) (40 g) in dimethoxyethane (DME) (CH3OCH2CH2OCH3) (1.39 Kg) and a mixture of Cashmeran™ (520 g) and ethyl formate (185 g) at room temperature. The mixture was stirred for 8 hours to provide 1,1,2,3,3-pentamethyl-4-oxo-2,3,4,5,6,7-hexahydro-1H-indene-5-carbaldehyde. Dimethylformamide (DMF) (300 mL) and hydroxylamine hydrochloride (NH2OH*HC1) (174 g) were then added and the temperature was heated to and maintained at 130° C. for 8 hours. Water was then added and the organic layer was extracted by toluene and washed once with water. Toluene was distilled off using a Rotovap to provide crude product 5,6,7,8-tetrahydro-6,6,7,8,8-pentamethyl-4H-indeno[5,4-D]isoxazole (260 g), which was then recrystallized to afford a pure product with a melting point of 80.96° C.

Workup

  1. customA 2 L reaction flask

Sources & evidence

ORD record
ord-d2f9d2b4052a4d4ea7398d18bad629d9
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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