Thioglycolic Acid → l-alpha-Methyl-8-methoxy-6,7-dihydroxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinoline
Reaction equation
[C:1]([O:6][CH2:7]C)(=O)[C:2]([CH3:4])=[CH2:3].[C:9]([O:14][CH2:15][CH2:16][OH:17])(=O)C(C)=C.[C:18]([OH:22])(=[O:21])[CH2:19]S.[CH3:23]C(N=NC(C#N)(C)C)(C#N)C.C([O:40][CH2:41][CH:42]1[O:44][CH2:43]1)(=O)C(C)=C.[CH3:45][N:46]([CH2:48][CH2:49]CCCCCCCCCC)C.[C:60]1(C)[CH:65]=CC=[CH:62][CH:61]=1>>[CH3:45][N:46]1[C@@H:4]([C@H:62]2[O:22][C:18](=[O:21])[C:19]3[C:15]([O:14][CH3:9])=[C:16]([O:17][CH3:23])[CH:65]=[CH:60][C:61]2=3)[C:2]2[C:3](=[CH:43][C:42]([OH:44])=[C:41]([OH:40])[C:1]=2[O:6][CH3:7])[CH2:49][CH2:48]1Participants
8
Reactant 7
Product 1
Procedure
A mixed solution of 90 g of ethyl methacrylate, 10 g of 2-hydroxyethyl methacrylate, 5 g of thioglycolic acid and 200 g of toluene was heated to 75° C. with stirring under nitrogen gas stream and, after adding thereto 1.0 g of AIBN, the reaction was carried out for 8 hours. Then, to the reaction mixture were added 8 g of glycidyl methacrylate, 1.0 g of N,N-dimethyldodecylamine and 0.5 g of tert-butylhydroquninone, and the resulting mixture was stirred for 12 hours at 100° C. After cooling, the reaction mixture was reprecipitated from 2 liters of n-hexane to obtain 82 g of the desired macromonomer as a white powder. The weight average molecular weight of the macromonomer obtained was 3.8×103. ##STR85##
Workup
- additionafter adding
- stirringthe resulting mixture was stirred for 12 hours at 100° C
- temperatureAfter cooling
- customthe reaction mixture was reprecipitated from 2 liters of n-hexane
- customto obtain 82 g of the desired macromonomer as a white powder
- customThe weight average molecular weight of the macromonomer obtained
Sources & evidence
- ORD record
- ord-4f63149b366f4a809a5e69a71ec7cc36
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05254422
Reaction notes
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