2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19922028, compound

HRID 327984Notes

Reaction equation

HRID 327984 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:49])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH2:36][C:37]([O:39]CC)=[O:38])=[O:29])[CH:25]=[CH:24][C:23]=1[O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]Br)C>CCCCCC.C(OCC)(=O)C>[C:37]([CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:28]([C:26]1[CH:25]=[CH:24][C:23]([O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][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:22]([CH2:21][CH2:20][C:19]([OH:49])=[O:18])[CH:27]=1)=[O:29])([OH:39])=[O:38]

Participants

4

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54464442HCID 54464442, compound

Product 1

HCID 19922028HCID 19922028, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Starting with 0.153 g (0.74 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, and 0.394 g (0.74 mmol) of 2-[(5-bromopentyl)oxy]-5-[[2-(2-ethoxy-2-oxoethyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester, the title compound (0.103 g, 26.7% overall yield) was obtained as a white solid, mp 105°-108.5° C. (recrystallized from hexane-ethyl acetate), using the procedure of example 22.

Sources & evidence

ORD record
ord-8449b81dcaac4d93af18005309c984be
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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