2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19921995, compound

HRID 1648060Notes

Reaction equation

HRID 1648060 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:17][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br>>[O:10]=[C:6]1[C:5]2[CH:11]=[CH:12][C:2]([O:1][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]([OH:36])=[O:17])=[C:3]([CH2:13][CH2:14][CH3:15])[C:4]=2[O:9][CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 53807823HCID 53807823, compound

Product 1

HCID 19921995HCID 19921995, compound

Procedure

Using the procedure of example 4, 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one was converted into the title compound by alkylation with 2-[(5-bromopentyl)oxy]benzenepentanoic acid methyl ester from the preceding example, followed by saponification, in 46.5% overall yield. The product was an off-white solid, mp 75°-76° C., recrystallized from hexane-ethyl acetate.

Sources & evidence

ORD record
ord-db72f52d3fe24ab4a2d085f355859584
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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