Water → 2'-(Ethoxycarbonyloxy)4,4',6'-trimethoxychalcone

HRID 364659

Reaction equation

Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].OC1C=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[C:9]=1[C:10](=[O:21])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[OH2:30].N1[CH:36]=[CH:35]C=CC=1>>[CH2:35]([O:3][C:2]([O:4][C:5]1[CH:6]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[C:9]=1[C:10](=[O:21])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[O:30])[CH3:36]

Participants

Reactant 4

HCID 962Water

HCID 1049Pyridine

HCID 10928Ethyl chloroformate

HCID 235736Flavokavain A

Product 1

HCID 537547452'-(Ethoxycarbonyloxy)4,4',6'-trimethoxychalconeYield 53%

Procedure

Ethyl chloroformate (216 mg) was added dropwise to a solution of 2'-hydroxy-4,4',6'-trimethoxychalcone (314 mg) in 5 ml of pyridine. After stirring at room temperature for 30 minutes, the mixture was poured into water (30 ml). The mixture was extracted with three 30 ml portions of chloroform, and the combined extracts were washed with water, dried over Na2SO4 and evaporated to give an oily residue. Crystallization of the residue from methanol gave 202 mg (53% yield) of 2'-(ethoxycarbonyloxy)4,4',6'-trimethoxychalcone as pale yellow prisms; m.p. 107° C.

Workup

extractionThe mixture was extracted with three 30 ml portions of chloroform
washthe combined extracts were washed with water
dry with materialdried over Na2SO4
customevaporated
customto give an oily residue
customCrystallization of the residue from methanol

Sources & evidence

ORD record: ord-886c005a8ab34ef0b612cdf910c5845e
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04605674

Linked notes

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