Stannane, tributyl(1-ethoxyethenyl)- → 9a-butyl-8-chloro-4-(1-ethoxyvinyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7882

Reaction equation

Br[C:2]1[C:3](=[O:22])[CH2:4][CH2:5][C:6]2([CH2:18][CH2:19][CH2:20][CH3:21])[C:14]=1[C:13]1[C:8](=[C:9]([Cl:17])[C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2.C([Sn](CCCC)(CCCC)[C:28]([O:30][CH2:31][CH3:32])=[CH2:29])CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:18]([C:6]12[CH2:5][CH2:4][C:3](=[O:22])[C:2]([C:28]([O:30][CH2:31][CH3:32])=[CH2:29])=[C:14]1[C:13]1[C:8](=[C:9]([Cl:17])[C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2)[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (90 mg, 0.235 mmol) in anhydrous toluene (1.2 mL) was treated with tributyl(1-ethoxyvinyl)stannane (0.111 mL, 0.352 mmol) and bis(triphenylphosphine)palladium(II) chloride (33 mg, 0.047 mmol). The mixture was placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 100° C. for 3 hours. After cooling to room temperature, the mixture was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates, developing with 5% EtOAc in CH2Cl2. The product band was eluted with EtOAc and the eluent evaporated under vacuum to afford 9a-butyl-8-chloro-4-(1-ethoxyvinyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (67 mg) as an oil.

Workup

temperatureAfter cooling to room temperature
customthe mixture was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates
washThe product band was eluted with EtOAc
customthe eluent evaporated under vacuum

Sources & evidence

ORD record: ord-6e31e21fba51466aaf8cfe2488e576b3
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Linked notes

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