Triphenylphosphine → Methyl 2-[2-[4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate

HRID 1294309Notes

Reaction equation

HRID 1294309 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH2:22][CH2:23][CH3:24])=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][C:33]([O:35][CH3:36])=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[C:1]1([C:7]2[O:8][C:9]([CH2:22][CH2:23][CH3:24])=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][O:21][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:18][CH:19]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68886296[4-[(2-Phenyl-5-propyl-4-oxazolyl)methoxy]phenyl]methanol

Product 1

HCID 68887693Methyl 2-[2-[4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetateYield 56%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]phenyl]methanol (0.50 g), methyl 2-(2-hydroxyphenyl)acetate (0.30 g), triphenylphosphine (0.60 g) and tetrahydrofuran (30 mL) was dropwise added a solution (40%, 1.00 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. To the reaction mixture was added ethyl acetate, and washed successively with water, a 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 2-[2-[4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate as an oil (0.40 g, 56%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. washwashed successively with water
  2. dry with materiala 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8f7ac54e63df413a8fac130eb9c7ac3a
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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