Triphenylphosphine → Methyl 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoate

HRID 1251908Notes

Reaction equation

HRID 1251908 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[OH:9])[CH:6]=1.[F:15][C:16]1[CH:34]=[CH:33][C:19]([CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:29](O)=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[O:9][C:29]2[CH:30]=[CH:31][C:22]([CH2:21][CH2:20][C:19]3[CH:18]=[CH:17][C:16]([F:15])=[CH:34][CH:33]=3)=[C:23]([CH:28]=2)[C:24]([O:26][CH3:27])=[O:25])[CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 183244462-(4-Methylimidazol-1-yl)-1-(thiazol-2-yl)ethanolHCID 18324453Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate

Product 1

HCID 18324416Methyl 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoateYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethanol (1.35 g, 6.46 mM), methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (1.95 g, 7.1 mM) and triphenylphosphine (1.86 g, 7.1 mM) in dry THF was cooled in an ice bath, and treated with DEAD (1.24 g, 7.1 mM). The mixture was allowed to warm to ambient temperature, stirred for 18 hours and evaporated to dryness. The product was purified on silica using methanol/dichloromethane (3→10%) as eluant to give methyl 5-[2-(4-methylimidazol-1-yl)-1-(thiazol-2-yl)ethoxy]-2-(4-fluorophenethyl)benzoate (1.45 g, 48%).

Workup

  1. temperaturewas cooled in an ice bath
  2. customevaporated to dryness
  3. customThe product was purified on silica

Sources & evidence

ORD record
ord-099796db366b411fa995b630272b4b02
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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