ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate → DA-E 5090

HRID 488130Notes

Reaction equation

HRID 488130 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:23]COC)=[C:6]([O:21][CH3:22])[CH:7]=[C:8]2/[CH:13]=[C:14](\[CH3:20])/[C:15]([O:17]CC)=[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]([OH:23])=[C:6]([O:21][CH3:22])[CH:7]=[C:8]2/[CH:13]=[C:14](/[CH3:20])\[C:15]([OH:17])=[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 6438615DA-E 5090Yield 53%

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-11add8b790ed4788b1b48b221183753c
Source dataset
uspto-grants-1994_03
Patent number
US05298649

Reaction notes

Loading…