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Potassium Carbonate → 4-(4-Chloro-but-2-ynoxy)-2-isopropylidenecoumaran-3-one

HRID 381681
Notes
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Reaction equation

HRID 381681 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:14])[C:5](=[C:11]([CH3:13])[CH3:12])[O:6]2.C(=O)([O-])[O-].[K+].[K+].[Cl:21][CH2:22][C:23]#[C:24][CH2:25]Cl>CN(C)C=O>[Cl:21][CH2:22][C:23]#[C:24][CH2:25][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:14])[C:5](=[C:11]([CH3:12])[CH3:13])[O:6]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131821,4-Dichloro-2-butyneHCID 183638364-Hydroxy-2-(propan-2-ylidene)-1-benzofuran-3(2H)-one

Product 1

HCID 183638464-(4-Chloro-but-2-ynoxy)-2-isopropylidenecoumaran-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.0 g 4-hydroxy-2-isopropylidenecoumaran-3-one, 4.6 g potassium carbonate, 3.3 ml 1,4-dichloro-but-2-yne and 100 ml dimethylformamide is warmed to 50° C. for 3 hours, then evaporated, mixed with water and extracted with dichloromethane. After evaporation of the extract, the residue (9.2 g) is purified by silica gel chromatography (eluent isohexane/ethyl acetate 9:1) to give 2.2 g of the desired intermediate.

Workup

  1. customevaporated
  2. additionmixed with water
  3. extractionextracted with dichloromethane
  4. customAfter evaporation of the extract
  5. customthe residue (9.2 g) is purified by silica gel chromatography (eluent isohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-aad3ab8d25e0497ea51d061d5aeebf55
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06307051B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes