2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19922084, compound

HRID 328006Notes

Reaction equation

HRID 328006 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:35])[CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br>>[O:10]=[C:6]1[C:5]2[CH:11]=[CH:12][C:2]([O:1][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][CH2:19][C:18]([OH:35])=[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 54161839HCID 54161839, compound

Product 1

HCID 19922084HCID 19922084, 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]benzenebutanoic acid methyl ester from the preceding example, followed by saponification, in 46.5% overall yield. The product was an off-white solid, mp 116°-118° C., recrystallized from acetonitrile.

Sources & evidence

ORD record
ord-3575cf5ac7334f3c917db6889482b1d3
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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