Potassium Carbonate → HCID 54437780, compound

HRID 328029Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][C:8](=[O:29])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=1)[CH3:2].[OH:31][C:32]1[CH:42]=[CH:41][C:35]2[C:36](=[O:40])[CH2:37][CH2:38][O:39][C:34]=2[C:33]=1[CH2:43][CH2:44][CH3:45].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][C:8](=[O:29])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:31][C:32]2[CH:42]=[CH:41][C:35]3[C:36](=[O:40])[CH2:37][CH2:38][O:39][C:34]=3[C:33]=2[CH2:43][CH2:44][CH3:45])=[C:11]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 89 °C

Procedure

A mixture of 0.43 g (0.89 mmol) of 4-(6-bromohexyl)-3-(3-ethoxy-3-oxopropyl)-δ-oxobenzenepentanoic acid ethyl ester from the preceding example, 0.188 g (0.91 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 0.398 g (2.88 mmol) of anhydrous granular potassium carbonate in 10 mL of 2-butanone was stirred and heated at 89° C. for 19.3 hr. The mixture was filtered with suction and the solid was washed with ether and ethyl acetate. The filtrate was concentrated in vacuo and the crude product was flash chromatographed on 80 g of silica gel, eluting with hexane-ethyl acetate (5:2). There was obtained 0.496 g (91.5%) of the title compound as a colorless oil.

Workup

filtrationThe mixture was filtered with suction
washthe solid was washed with ether and ethyl acetate
concentrationThe filtrate was concentrated in vacuo
customchromatographed on 80 g of silica gel
washeluting with hexane-ethyl acetate (5:2)

Sources & evidence

ORD record: ord-2833ac1c4754499da2aaccda254a8cf0
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273999

Reaction notes

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