Tributylvinyltin → HCID 21107234, compound

HRID 1870002Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:15][CH3:16])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][C:7]2([CH3:14])[CH3:13].[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC>CN(C)C=O.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>[CH3:16][O:15][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([CH:17]=[CH2:18])[CH:3]=1)[C:10](=[O:12])[CH2:9][CH2:8][C:7]2([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 91 °C

Procedure

A solution of 8-bromo-6-methoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 154, 2.83 g, 10 mmol) and tributyl(vinyl)tin (3 mL, 10 mmol) in anhydrous N,N-dimethyl formamide (30 mL) was sparged with argon and treated with tetrakis(triphenylphosphine)palladium (0) (0.3 g, 0.26 mmol). The resulting reaction mixture was heated to 91° C. for two days at the end of which it was cooled to ambient temperature, diluted with water and extracted with diethyl ether (×2). The combined organic phase was washed with water (×1), and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated to a pale yellow oil. Flash chromatography using 15% ethyl acetate in hexane as the eluent afforded the title product (1.7 g, 73%) as a pale yellow oil.

Workup

customThe resulting reaction mixture
temperaturewas cooled to ambient temperature
extractionextracted with diethyl ether (×2)
washThe combined organic phase was washed with water (×1), and brine (×1)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated to a pale yellow oil

Sources & evidence

ORD record: ord-d3b478427fc343f69062f08a6baf0a10
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638648B2

Reaction notes

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