Triphenylphosphine → HCID 67757677, compound

HRID 2225800Notes

Reaction equation

HRID 2225800 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([CH:18]([CH3:20])[CH3:19])[C:9]=2/[CH:21]=[CH:22]/[CH2:23][OH:24])=[CH:4][CH:3]=1.[CH3:25][O:26][C:27](=[O:37])[C:28]([C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1)=[O:29].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:25][O:26][C:27](=[O:37])[C:28](=[O:29])[C:30]1[CH:31]=[CH:32][C:33]([O:24][CH2:23]/[CH:22]=[CH:21]/[C:9]2[C:10]([CH:18]([CH3:20])[CH3:19])=[N:11][C:12]3[C:17]([C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 14780566HCID 14780566, compound

Product 1

HCID 67757677HCID 67757677, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 15, (E)-3-[4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl]-2-propen-1-ol (1.0 g) was coupled with 4-hydroxyphenylglyoxylic acid methyl ester (0.565 g) in the presence of diethyl azodicarboxylate (0.683 g) and triphenylphosphine (1.02 g) in tetrahydrofuran (30 mL). The usual work up, followed by purification of the crude product by flash chromatography over silica gel (50 g; diethyl ether-hexane; 1:4) and crystallization from diethyl ether to provide 0.94 g of (E)-4-[3-[4-(4-fluorophenyl)-2-(1-methylethyl)-3-quinolinyl]-2-propenyloxy]-alpha-oxobenzeneacetic acid methyl ester, mp 109°-111° C.

Workup

  1. customThe usual work up, followed by purification of the crude product by flash chromatography over silica gel (50 g; diethyl ether-hexane; 1:4) and crystallization from diethyl ether

Sources & evidence

ORD record
ord-3a1f7cf5b727473db74a432030da7d65
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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