Sodium Carbonate → 4-{2-[4-(t-Butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazol-4-yl]ethyl}-biphenyl-4-carbaldehyde

HRID 1375924Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][O:13][C:12]([CH3:15])=[N:11]2)=[CH:4][CH:3]=1.[C:25]([O-:28])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.CCOC(C)=O.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>[Si:18]([O:17][CH2:16][C:10]1([CH2:9][CH2:8][C:5]2([CH:25]=[O:28])[CH:6]=[CH:7][C:2]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:3][CH2:4]2)[CH2:14][O:13][C:12]([CH3:15])=[N:11]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of 4-[2-(4-bromophenyl)ethyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole (2 mmol), 4-fomylphenylboronic acid (2.4 mmol), Pd(PPh3)4 (0.2 mmol) and Na2CO3 (9.6 mmol) in toluene (5 mL), EtOH (1.5 mL) and H2O (5 mL) is stirred at 90° C. for 5 h. It is diluted with H2O (15 mL) and EtOAc (15 mL) and the organic phase is washed with brine and dried over Na2SO4. After concentration, the crude product is purified by column chromatography using EtOAc/hexane (1/4) to give the desired product as a white solid. MS: (ES+): 438.2 (M+1)+.

Workup

washthe organic phase is washed with brine
dry with materialdried over Na2SO4
concentrationAfter concentration
customthe crude product is purified by column chromatography

Sources & evidence

ORD record: ord-e8980b17e19044bab5848ac7399bd71e
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169817B2

Reaction notes

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