Ethyl Acetate → t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene

HRID 964456

Reaction equation

[CH2:1]([Li])CCC.[Si:6]([O:13][C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([CH:23]=O)=[CH:16][C:15]=1[CH2:25][CH2:26][CH3:27])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[Si:6]([O:13][C:14]1[C:19]([CH2:20][CH2:21][CH3:22])=[CH:18][C:17]([CH:23]=[CH2:1])=[CH:16][C:15]=1[CH2:25][CH2:26][CH3:27])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.0 g (2.80 mmol) of methyl triphenylphosphonium bromide in 5.0 mL of ether at 0° C. was added 1.12 mL (2.5M, 2.80 mmol) of butyllithium. The reaction mixture was stirred for 30 minutes at 0° C. and then 756 mg (2.33 mmol) of the title compound from Example 14 (Step A) was added. After stirring for 1 h at room temperature, the reaction mixture was poured into ethyl acetate and washed with water and then saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography (silica gel, hexane/ethyl acetate 97:3) gave 411 mg of the title compound.

Workup

stirringAfter stirring for 1 h at room temperature
washwashed with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by flash chromatography (silica gel, hexane/ethyl acetate 97:3)

Sources & evidence

ORD record: ord-7aafbc6acb47421ba92d69dc5da41655
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767310

Linked notes

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