2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19921929, compound

HRID 1648034Notes

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].C([O:18][C:19](=[O:48])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([O:38]CC)=[O:37])[CH:31]=2)=[O:29])[CH:25]=[CH:24][C:23]=1/[CH:41]=[CH:42]/[CH2:43][CH2:44][CH2:45][CH2:46]Br)C>>[C:36]([C:32]1[CH:31]=[C:30]([C:28]([C:26]2[CH:25]=[CH:24][C:23](/[CH:41]=[CH:42]/[CH2:43][CH2:44][CH2:45][CH2:46][O:1][C:2]3[CH:12]=[CH:11][C:5]4[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=4[C:3]=3[CH2:13][CH2:14][CH3:15])=[C:22]([CH2:21][CH2:20][C:19]([OH:48])=[O:18])[CH:27]=2)=[O:29])[CH:35]=[CH:34][CH:33]=1)([OH:38])=[O:37]

Participants

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one

HCID 67780240HCID 67780240, compound

Product 1

HCID 19921929HCID 19921929, compound

Procedure

Starting with 0.242 g (1.17 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 0.604 g (1.17 mmol) of (E)-2-(6-bromo-1-hexenyl)-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester, the title compound was obtained (97 mg; 15.8% overall yield) as a white solid, mp 105°-109° C. (recrystallized from hexane-ethyl acetate), using the procedure of example 22.

Sources & evidence

ORD record: ord-f8597ae352c842ec87ed28cefc918f3c
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05434186

Reaction notes

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