Ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate → Ethyl 4-(4-chloro-2-nitrophenyl)-4-oxo-2-butynoate

HRID 428449Notes

Reaction equation

HRID 428449 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:16])[C:9]#[C:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]#[C:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

4

Reactant 1

HCID 18358875Ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate

Product 1

HCID 18358889Ethyl 4-(4-chloro-2-nitrophenyl)-4-oxo-2-butynoateYield 51.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate(7.46 g, 26.3 mmoles) in dichloromethane (350 mL) cooled in an ice-bath was added manganese dioxide (26.2 g, 301.3 mmol). The reaction mixture was stirred for 20 minutes and then was allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 130 minutes and then was filtered twice through a pad of CELITE™. The filtrate was purified by flash chromatography on silica gel (195 g), eluting with dichloromethane, to afford 3.80 g (51%) of the title compound as a brownish-orange oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 130 minutes
  2. filtrationwas filtered twice through a pad of CELITE™
  3. customThe filtrate was purified by flash chromatography on silica gel (195 g)
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-46f9017651ab4aa0b0dc26fa4db33aec
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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