Diazomethane diethylether → methyl 1-(4-(N-methylaminosulfonyl)phenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetate

HRID 542227Notes

Reaction equation

HRID 542227 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:13]2[CH3:28])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N+](=[CH2:31])=[N-].CCOCC>CO>[CH3:31][NH:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:13]2[CH3:28])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 21186548Diazomethane diethyletherHCID 70401818methyl 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetate

Product 1

HCID 67583673methyl 1-(4-(N-methylaminosulfonyl)phenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetateYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4a (100 mg) in methanol (20 ml) was treated with excess diazomethane ether solution to give two products. They are separated via preparative tlc using 1500 μm silica gel plates developed 3 times with 5% ethyl acetate in chloroform to give Z methyl 1-(4-(N-methylaminosulfonyl)phenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetate (6a) (30 mg, 29% yield): m.p. 167°-169° C.

Workup

  1. customto give two products
  2. customThey are separated via preparative tlc

Sources & evidence

ORD record
ord-444feaece30a4ad5bb8930ec7d2f63d3
Source dataset
uspto-grants-1987_04
Patent number
US04656190

Reaction notes

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