Diethyl Malonate → HCID 10020292, compound

HRID 1940974Notes

Reaction equation

HRID 1940974 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=O.ClC1C=CC(OC)=CC=1.C1(C)C(C(Cl)=O)=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:41](OCC)(=[O:48])[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].N12CCCN=C1CCCCC2>ClC(Cl)C(Cl)Cl>[CH2:46]([O:45][C:43]([C:42]1[C:41](=[O:48])[O:17][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][C:6]=2[C:7]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:44])[CH3:47]

Participants

8

Reactant 6

HCID 7761Diethyl MalonateHCID 121674-ChloroanisoleHCID 702762-Methylbenzoyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6451240Aluminum(III) ChlorideHCID 21463072HCID 21463072, compound

Product 1

HCID 10020292HCID 10020292, compound

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

A mixture of 5-Chloro-2-hydroxy-2'-methylbenzophenone [prepared by reaction of 4-chloroanisole with ortho-toluoyl chloride in 1,1,2,2,-tetrachloroethane in the presence of aluminum chloride (150° C., 7 hours): melting point 65°-66° C.](71.9g), diethyl malonate (70 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4 ml) was stirred at 170° C. for 6 hours. The reaction mixture was purified by silica gel column chromatography (hexane) to yield 6-chloro-4-(2-methylphenyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester as colorless crystals (73.2 g).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-154f554cd2e64c84b2d039c1cee55f54
Source dataset
uspto-grants-1997_12
Patent number
US05700810

Reaction notes

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