HCID 23050479, compound → HCID 23050463, compound

HRID 1651835Notes

Reaction equation

HRID 1651835 reaction equation
[OH:1][CH:2]([C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[C:3]#[C:4][C:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:6]>C(Cl)Cl>[CH3:26][O:25][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[O:23][CH3:24])[C:2]([C:3]#[C:4][C:5]([O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:6])=[O:1]

Participants

3

Reactant 1

HCID 23050479HCID 23050479, compound

Product 1

HCID 23050463HCID 23050463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8.5 g (23 mmol) of 2-(2-methoxyethoxy)-ethyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate in 100 ml of methylene chloride was added dropwise at 0° to a suspension of 60 g (0.69 mol) of manqanese dioxide in 150 ml of methylene chloride. The reaction mixture was stirred at 0° for 2 hours, filtered over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 700 g of silica gel (elution agent methylene chloride/ether 4:1) and subsequently crystallized from ether/hexane. There was obtained 2-(2-methoxyethoxy)ethyl 3-(3,4,5-trimethoxybenzoyl)propiolate of melting point 33°-34°.

Workup

  1. filtrationfiltered over magnesium sulphate
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on 700 g of silica gel (elution agent methylene chloride/ether 4:1)
  4. customsubsequently crystallized from ether/hexane

Sources & evidence

ORD record
ord-fe8f7d469e8c413d944387ef096959f4
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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