4-[2-(4-Bromophenyl)vinyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole → HCID 69430585, compound

HRID 1375923Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH: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(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Br:1][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

Participants

Conditions

Temperature: 40 °C

Procedure

4-[2-(4-Bromophenyl)vinyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole (3 mmol) is dissolved in ethanol (15 mL) and hydrogenated at atmospheric pressure in the presence of chlorotris(triphenylphosphine)rhodium(I) (10%). The mixture is stirred at 40° C. for 12 h. After filtration and concentration, the crude product is obtained as colorless oil, which is used directly in the next step without further purification. MS: (ES+): 412.1 (M+1)+.

Workup

filtrationAfter filtration and concentration

Sources & evidence

ORD record: ord-55a55965677246899646a33806a3884b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169817B2

Reaction notes

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