2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19921914, compound

HRID 1648025Notes

Reaction equation

HRID 1648025 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:45])[CH2:20][CH2:21][CH2:22][C:23](=[O:44])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)=[C:26]([CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])[CH:25]=1)C>CCCCCC.C(OCC)(=O)C>[C:39]([CH2:38][CH2:37][C:26]1[CH:25]=[C:24]([C:23](=[O:44])[CH2:22][CH2:21][CH2:20][C:19]([OH:45])=[O:18])[CH:29]=[CH:28][C:27]=1[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][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])([OH:41])=[O:40]

Participants

4

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54205626HCID 54205626, compound

Product 1

HCID 19921914HCID 19921914, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Starting with 0.135 g (0.66 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, and 0.31 g (0.64 mmol) of 4-[(5-bromopentyl)oxy]-3-(3-ethoxy-3-oxopropyl)-δ-oxobenzenepentanoic acid ethyl ester, the title compound (0.190 g; 62.8% overall yield) was obtained as a white solid, mp 151°-153.5° C. (recrystallized from hexane-ethyl acetate), using the procedure of example 22.

Sources & evidence

ORD record
ord-973a333e2ee84395972da5299b9f42da
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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