Triphenylphosphine → Methyl phenylglyoxalate

HRID 2225804Notes

Reaction equation

HRID 2225804 reaction equation
FC1C=CC(C2C3C(=CC=CC=3)N(C(C)C)C=2/C=C/CO)=CC=1.[CH3:24][O:25][C:26](=[O:36])[C:27]([C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)=[O:28].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:24][O:25][C:26](=[O:36])[C:27](=[O:28])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004348HCID 19004348, compound

Product 1

HCID 84835Methyl phenylglyoxalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 15, (E)-3-[3-(4-fluorophenyl)-1-(1-methylethyl)- 1H-indol-2-yl]-2-propen-1-ol (1.0 g) was reacted with 4-hydroxyphenylglyoxylic acid methyl ester (0.585 g) in the presence of diethyl azodicarboxylate (0.71 g) and triphenylphosphine (1.06 g) in tetrahydrofuran (30 mL). The crude reaction product, isolated in the usual manner, was purified by flash chromatography over silica gel (130 g; ethyl acetate-hexane; 1:4) to furnish 0.61 g of (E)-4-[3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-2-yl]-2-propenyloxy]-alpha-oxobenzeneacetic acid methyl ester as a yellow oil. A portion (0.2 g) was rechromatographed over silica gel (diethyl ether-hexane; 1:19) to furnish 0.225 g of the analytically pure ester as an oil.

Workup

  1. customThe crude reaction product
  2. customisolated in the usual manner
  3. customwas purified by flash chromatography over silica gel (130 g; ethyl acetate-hexane; 1:4)

Sources & evidence

ORD record
ord-4d4b188013594d9e88d5e76000c37c4a
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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