1,1-Dimethoxyethyl(dimethyl)amine → HCID 54134676, compound

HRID 2371814Notes

Reaction equation

HRID 2371814 reaction equation
O[CH:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[C:12]2[CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[CH:7][CH:6]=1)[CH:3]=[CH2:4].CO[C:30]([O:35]C)([N:32]([CH3:34])[CH3:33])[CH3:31]>C1(C)C=CC=CC=1>[CH3:34][N:32]([CH3:33])[C:30]([CH2:31][CH2:4][CH:3]=[CH:2][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[C:12]2[CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[CH:7][CH:6]=1)=[O:35]

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 19906383HCID 19906383, compound

Product 1

HCID 54134676HCID 54134676, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-[7-(1-hydroxyallyl)naphth-1-ylmethyl]-3-methoxybenzoate (2.4 g), N,N-dimethylacetamide dimethyl acetal (1.62 ml) and toluene (50 ml) was refluxed for 12 hours. Evaporation and flash chromatgraphy, eluting with a gradient of 1) 3:3:2 petroleum ether:methylene chloride:ethyl acetate, 2) 1:1:1 petroleum ether:methylene chloride:ethyl acetate, and 3) 6:6:7 petroleum ether:methylene chloride:ethyl acetate, afforded methyl 4-[7-[4-(dimethylcarbamoyl)but-1-enyl]naphth-1-ylmethyl]-3-methoxybenzoate (90%) as a light yellow syrup; MS(CI), m/e=432(M+H).

Workup

  1. temperaturewas refluxed for 12 hours
  2. customEvaporation and flash chromatgraphy
  3. washeluting with a gradient of 1) 3:3:2 petroleum ether

Sources & evidence

ORD record
ord-733eb90704404e898831929dd35e3597
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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