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Potassium Carbonate → HCID 54437780, compound

HRID 1648089
Notes
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Reaction equation

HRID 1648089 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54373749HCID 54373749, compound

Product 1

HCID 54437780HCID 54437780, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

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

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

Sources & evidence

ORD record
ord-e8473350da214c17b7578c75bd05739d
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05434186

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes