2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19922008, compound

HRID 327958Notes

Reaction equation

HRID 327958 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:38])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]OS(C)(=O)=O>CCCCCC.C(OCC)(=O)C>[O:10]=[C:6]1[C:5]2[CH:11]=[CH:12][C:2]([O:1][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][C:18]([OH:38])=[O:17])=[C:3]([CH2:13][CH2:14][CH3:15])[C:4]=2[O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54168313HCID 54168313, compound

Product 1

HCID 19922008HCID 19922008, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using the procedure of example 11 and starting with 0.2 g (1 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 0.32 g (1 mmol) of 2-[6-[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester (from example 36), 2-[6-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]hexyl]benzenepropanoic acid was obtained in 45.6% overall yield, as a colorless solid, mp 98°-99° C. (recrystallized from hexane-ethyl acetate).

Sources & evidence

ORD record
ord-1ec59c414f4748b7a14366ae5269f468
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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