Triphenylphosphine → HCID 53676059, compound

HRID 2225790Notes

Reaction equation

HRID 2225790 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][O:13][C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH2:16][CH3:17].[CH3:21][O:22][C:23](=[O:33])[C:24]([C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:21][O:22][C:23](=[O:33])[C:24](=[O:25])[C:26]1[CH:27]=[CH:28][C:29]([O:1][CH2:2][C:3]#[C:4][C:5]2[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:12][O:13][C:14](=[O:20])[C:15]([CH3:19])([CH3:18])[CH2:16][CH3:17])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 54389298HCID 54389298, compound

Product 1

HCID 53676059HCID 53676059, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 2,2-dimethylbutanoic acid [2-(3-hydroxy-1-propynyl)-3-methylphenyl]methyl ester (1.05 g), 4-hydroxyphenylglyoxylic acid methyl ester (0.693 g) and triphenylphosphine (1.26 g) in tetrahydrofuran (30 mL) was cooled to 0° C., and a solution of diethyl azodicarboxylate (0.76 mL) in tetrahydrofuran (5 mL) was added over 5 minutes. The reaction mixture was stirred at 0° C. for 1 hour then at room temperature overnight. The solvent was evaporated and the residue triturated with diethyl ether to remove most of the triphenylphosphine oxide. The filtrate was concentrated in vacuo and the resulting oil was chromatographed over silica gel (10 g; diethyl ether-hexane; 1:19) to furnish 1.4 g of 4-[3-[2-[(2,2-dimethyl-1-oxobutoxy) methyl]-6-methylphenyl]-2-propynyloxy]-alpha-oxobenzeneacetic acid methyl ester as a colorless oil.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solvent was evaporated
  4. customthe residue triturated with diethyl ether
  5. customto remove most of the triphenylphosphine oxide
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting oil was chromatographed over silica gel (10 g; diethyl ether-hexane; 1:19)

Sources & evidence

ORD record
ord-d2b117a44973401ebe37268cad91bac4
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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