Methanol → HCID 68884746, compound

HRID 1294252Notes

Reaction equation

HRID 1294252 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.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)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>[CH3:28][C:27]1[O:26][C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:24][C:23]=1[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C:5]2[CH:4]=[CH:3][C:2]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:7][C:6]=2[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 68883486Methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate

Product 1

HCID 68884746HCID 68884746, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-[5-bromo-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate (1.20 g), phenylboronic acid (0.30 g), tetrakis(triphenylphosphine)palladium (0.14 g), 2M aqueous sodium carbonate solution (3.7 mL), methanol (5 mL), and toluene (20 mL) were stirred with heating under reflux for 24 hrs under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration of the organic layer, the residue was subjected to silica gel column chromatography to give crystals (0.89 g, 74%) of methyl 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-5-phenylphenyl]acetate from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 111-112° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 24 hrs under an argon atmosphere
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-490a328b348a413aaf999905a771fc20
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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