Triphenylphosphine → HCID 23282603, compound

HRID 369879Notes

Reaction equation

HRID 369879 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([C:16](=[O:19])[CH2:17]Br)[CH:13]=[CH:12][C:4]=1[O:5][CH2:6][C:7]([O:9]CC)=[O:8].[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:15]=[C:14]([CH:13]=[CH:12][C:4]=1[O:5][CH2:6][C:7]([OH:9])=[O:8])[C:16]([CH:17]=[P:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:19]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 23282573HCID 23282573, compound

Product 1

HCID 23282603HCID 23282603, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To chloroform (200 ml) are added ethyl α-[2-methoxy-4-(2-bromoacetyl)phenoxy]acetate (20 g) and triphenylphosphine (20.6 g) in an ice-bath, and the mixture is stirred for one hour. After confirming that the starting compounds are well consumed, the mixture is washed with an aqueous potassium carbonate solution. The mixture is dried over magnesium sulfate, and concentrated under reduced pressure to remove the solvent. To the residue is added methanol (200 ml), and thereto is added dropwise sodium hydroxide in an ice-bath. After confirming that the starting compounds are well consumed, to the mixture is added conc hydrochloric acid. The precipitated crystals are washed with water and diethyl ether, and dried to give (3-methoxy-4-carboxymethoxybenzoyl)methylenetriphenylphosphorane (25 g).

Workup

  1. customare well consumed
  2. washthe mixture is washed with an aqueous potassium carbonate solution
  3. dry with materialThe mixture is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent
  6. additionTo the residue is added methanol (200 ml)
  7. additionis added dropwise sodium hydroxide in an ice-bath
  8. customare well consumed, to the mixture
  9. additionis added conc hydrochloric acid
  10. washThe precipitated crystals are washed with water and diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-4a568c6c5f1e4284ba63fc688e1e5a7c
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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