Tetramethyltin → HCID 68887628, compound

HRID 1294245Notes

Reaction equation

HRID 1294245 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][C:27]=3[CH3:28])=[CH:17][CH:16]=2)=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:7]=1.[CH3:35][Sn](C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:35][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[O:26][C:27]=3[CH3:28])=[CH:19][CH:20]=2)=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 68883486Methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate

Product 1

HCID 68887628HCID 68887628, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate (1.00 g), tetramethyltin (0.73 g), tetrakis(triphenylphosphine)palladium (0.11 g) and toluene (50 mL) were stirred with heating under reflux under an argon atmosphere for 40 hrs. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography to give crystals (0.28 g, 32%) of methyl 2-[5-methyl-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 80-81° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux under an argon atmosphere for 40 hrs
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-79a72f267ffa44a48059cee657707787
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…