2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 54554587, 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].[CH2:16]([O:18][C:19](=[O:48])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=[CH:24][C:23]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]OS(C)(=O)=O)[CH3:17]>>[CH2:16]([O:18][C:19](=[O:48])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([O:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:25]=[CH:24][C:23]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][O: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])[CH3:17]Participants
Procedure
Using the procedure of example 11 and starting with 0.28 g (1.4 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 0.7 g (1.4 mmol) of 2-[5-(methylsulfonyl)oxypentyloxy]-5-(3-ethoxycarbonylpropoxy)benzenepropanoic acid ethyl ester (from example 46), 5-(3-ethoxycarbonylpropoxy)-2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]benzenepropanoic acid ethyl ester was obtained in 83.6% yield (0.7 g) as a solid. This diester (1.17 mmol) was saponified with 3 mL of 3N aqueous lithium hydroxide in 25 mL of tetrahydrofuran, at room temperature, for 37 hr. Work-up as in example 4gave a light-brown oily acid which was flash-chromatographed on silica gel, eluting with 95:5:1 chloroform-methanol-acetic acid. There was obtained 0.39 g (61.5%) of pure 5-(3-carboxypropoxy)-2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy] benzenepropanoic acid. Recrystallization from hexane-ethyl acetate gave a colorless solid, mp 119°-124° C.
Sources & evidence
- ORD record
- ord-8288e571d2f4464a93e2a921f89f79cc
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273999
Reaction notes
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