2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 67780161, compound
Reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[CH2:13][CH2:14][CH3:15].[CH3:16][O:17][C:18](=[O:46])[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]OS(C)(=O)=O)=[C:25](/[CH:40]=[CH:41]/[C:42]([O:44]C)=[O:43])[CH:24]=1>>[CH3:16][O:17][C:18](=[O:46])[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:1][C:2]2[CH:12]=[CH:11][C:5]3[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=3[C:3]=2[CH2:13][CH2:14][CH3:15])=[C:25](/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43])[CH:24]=1Participants
Procedure
Using the procedure of example 11 and starting with 0.26 g (1.3 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 0.76 g (1.3 mmol) of (E)-4-[3-(3-methoxy-3-oxo-1-propenyl)-4-[6-[(methylsulfonyl)oxy]hexyl]phenoxy]butanoic acid methyl ester (from example 113), (E)-4-[3-(2-carboxyethenyl)-4-[6[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]hexyl]phenoxy]butanoic acid methyl ester was obtained in 95% yield (0.36g) as a colorless oil which crystallized on standing. Recrystallization from ethyl acetate-hexane gave 0.51 g (69%) of a colorless solid, mp 65°-66° C. A 0.2 g (0.35 mmol) sample of diester prepared in this way was saponified with 2 mL of 3N aqueous lithium hydroxide in 10 mL of tetrahydrofuran, at room temperature, for 22 hr. Work-up as in example 4 gave a crude acid product which was purified by chromatography on silica gel (toluene-ethyl acetate containing 2% acetic acid) and recrystallization from acetonitrile. There was obtained 0.1 g (53%) of (E)-4-[3-(2-carboxyethenyl)-4-[6-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]hexyl]phenoxy]butanoic acid as an off-white solid mp 140°-143° C.
Sources & evidence
- ORD record
- ord-b043175ffa0a4e8f92429c9902872b86
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273999
Reaction notes
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