Ethanol → HCID 22922427, compound

HRID 2258505Notes

Reaction equation

HRID 2258505 reaction equation
[OH:1][CH:2]1[C:8]([CH3:10])([CH3:9])[CH2:7][C:6](=[O:11])[C:5]([CH3:12])=[CH:4][CH:3]1[O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[CH2:25](O)[CH3:26]>>[CH2:25]([O:11][C:6]12[O:1][CH:2]([C:8]([CH3:9])([CH3:10])[CH2:7]1)[CH:3]([O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH:4]=[C:5]2[CH3:12])[CH3:26]

Participants

3

Reactant 2

HCID 702EthanolHCID 22922369HCID 22922369, compound

Product 1

HCID 22922427HCID 22922427, compoundYield 64%

Procedure

5-Hydroxy-4-(4-nitrobenzoyloxy)-2,6,6-trimethyl-2-cyclohepten-1-one (1.00 g, 3.0 mM) obtained in Example 44 was treated with ethanol (20 ml) according to the procedures described in Example 99 and crystallized from a mixed solution of ethyl acetate and hexane to obtain 0.7 g (64%) of 1-ethoxy-4-(4-nitrobenzoyloxy)-2,6,6-trimethyl-8-oxabicyclo[3.2.1]oct-2-ene (AU246) as light yellow flakes. Melting point: 144° to 146° C.

Workup

  1. customcrystallized from a mixed solution of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a5d684847db54b08b76e10ac101fdca2
Source dataset
uspto-grants-1997_08
Patent number
US05661166

Reaction notes

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