ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate → Ethyl (Z)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate

HRID 654707Notes

Reaction equation

HRID 654707 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:23][CH2:24][O:25][CH3:26])=[C:6]([O:21][CH3:22])[CH:7]=[C:8]2/[CH:13]=[C:14](\[CH3:20])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2]>CC(C)=O>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:23][CH2:24][O:25][CH3:26])=[C:6]([O:21][CH3:22])[CH:7]=[C:8]2/[CH:13]=[C:14](/[CH3:20])\[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2]

Participants

3

Reactant 1

HCID 9975669ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate

Product 1

HCID 10316348Ethyl (Z)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoateYield 42.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15.6 g of ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate was dissolved in 300 ml of acetone and irradiated for 2 hours with light from a high pressure mercury lamp through a Pyrex filter. The solvent was evaporated and the resultant residue was purified by silica gel column chromatography (3% ethyl acetate/hexane) to obtain 6.6 g of the titled compound as a yellow oil. At the same time, 9.0 g of a mixture of E and Z isomers was obtained.

Workup

  1. customirradiated for 2 hours with light from a high pressure mercury lamp through a Pyrex
  2. filtrationfilter
  3. customThe solvent was evaporated
  4. customthe resultant residue was purified by silica gel column chromatography (3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3ea15692b3d146729868622727537779
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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