Triphenylphosphine → HCID 67756672, compound

HRID 2225793Notes

Reaction equation

HRID 2225793 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/[CH:17]=[CH: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].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]/[CH:18]=[CH:17]/[C:9]2[C:10]([CH:14]([CH3:16])[CH3:15])=[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

5

Reactant 3

HCID 11776TriphenylphosphineHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004503HCID 19004503, compound

Product 1

HCID 67756672HCID 67756672, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 15, (E)-3-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yl]-2-propen-1-ol (0.58 g) was reacted with 4-hydroxyphenylglyoxylic acid methyl ester (0.387 g) in the presence of diethyl azoclicarboxylate (0.448 g) and triphenylphosphine (0.68 g) in tetrahydrofuran (25 mL). The usual work up afforded 1.3 g of a crude mixture that was purified by flash chromatography over silica gel (130 g; ethyl acetate-hexane; 3:7) to furnish 0.55 g of (E)-4-[3-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yl]-2-propenyloxy]-alpha-oxobenzeneacetic acid methyl ester as a oil.

Workup

  1. customThe usual work up afforded 1.3 g of a crude mixture that
  2. customwas purified by flash chromatography over silica gel (130 g; ethyl acetate-hexane; 3:7)

Sources & evidence

ORD record
ord-31ee1163230643bfbada8b2172f1e37a
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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