Triphenylphosphine → 4-[2-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225798Notes

Reaction equation

HRID 2225798 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[C:9]=2[O:17][CH2:18][CH2:19][OH:20])=[CH:4][CH:3]=1.[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].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:21][O:22][C:23](=[O:33])[C:24](=[O:25])[C:26]1[CH:27]=[CH:28][C:29]([O:20][CH2:19][CH2:18][O:17][C:9]2[C:10]([CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=[CH:13][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 190044172-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethanol

Product 1

HCID 545175004-[2-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid methyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 15, (2-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethanol (0.393 g) was treated with 4-hydroxyphenylglyoxylic acid methyl ester (0.258 g) in the presence of diethyl azodicarboxylate (0.298 g) and triphenylphosphine (0.449 g) in tetrahydrofuran (25 mL). The usual work up afforded 0.6 g of crude product which was purified by flash chromatography over silica gel (60 g; ethyl acetate-hexane; 3:7) to furnish 0.3 g of 4-[2-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethoxy]-alpha-oxobenzeneacetic acid methyl ester. Crystallization of the ester from ethyl acetatehexane yielded the analytical specimen, mp 77°-79° C.

Workup

  1. customThe usual work up afforded 0.6 g of crude product which
  2. customwas purified by flash chromatography over silica gel (60 g; ethyl acetate-hexane; 3:7)

Sources & evidence

ORD record
ord-87cd802bf7034d929f9ebc28b62d6a1c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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