6-Hydroxy-5-propyl-3,4-dihydro-2H-naphthalen-1-one → 2-[(5-Carboxypentyl)oxy]-6-[6-[(5,6,7,8-tetrahydro-5-oxo-1-propyl-2-naphthalenyl)oxy]hexyl]benzenepropanoic Acid
Reaction equation
[OH:1][C:2]1[C:3]([CH2:13][CH2:14][CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C[O:17][C:18](=[O:48])[CH2:19][CH2:20][C:21]1[C:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]OS(C)(=O)=O)=[CH:25][CH:24]=[CH:23][C:22]=1[O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46]C)=[O:45]>>[C:44]([CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=3[C:3]=2[CH2:13][CH2:14][CH3:15])[C:21]=1[CH2:20][CH2:19][C:18]([OH:48])=[O:17])([OH:46])=[O:45]Participants
3
Reactant 2
Product 1
Procedure
Using the procedure of example 184, 6-hydroxy-5-propyl-1,2,3,4-tetrahydronaphthalen-1-one from example 9 was converted into the title compound by alkylation with 2-[(6-methoxy-6-oxohexyl)oxy]-6-[6-[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester from example 156, followed by saponification, in 68% overall yield. The diacid product was a colorless solid, mp 100°-101° C., recrystallized from hexane-ethyl acetate.
Sources & evidence
- ORD record
- ord-c3cfe4ee3f9243f68f19c6aa30db1464
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05434186
Reaction notes
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