Stannane, tributyl[4-(methoxymethoxy)phenyl]- → 9a-butyl-7-methoxy-4-(4-methoxymethoxy-phenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7838

Reaction equation

Br[C:2]1[C:3](=[O:21])[CH2:4][CH2:5][C:6]2([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=1[C:13]1[C:8](=[CH:9][C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2.C([Sn](CCCC)(CCCC)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=1)CCC>C1(C)C=CC=CC=1.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>[CH2:17]([C:6]12[CH2:5][CH2:4][C:3](=[O:21])[C:2]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=3)=[C:14]1[C:13]1[C:12](=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:7]2)[CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (800 mg, 2.29 mmol), Pd(PPh3)4 (132 mg, 0.114 mmol), and tributyl-(4-methoxymethoxy-phenyl)-stannane (1.174 g, 2.75 mmol) in anhydrous toluene (11.5 mL) was placed under a nitrogen atmosphere and heated with stirring in an oil bath at 100° C. After 22 hours, the mixture was cooled to room temperature and evaporated under vacuum to a dark oil (2.208 g). This material was purified by chromatography on EM silica gel 60 (230-400 mesh, 115 mL dry), using 4:1 hexanes-EtOAc as eluting solvent, to afford 9a-butyl-7-methoxy-4-(4-methoxymethoxy-phenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (787 mg) as a yellow gum.

Workup

temperatureheated
temperaturethe mixture was cooled to room temperature
customevaporated under vacuum to a dark oil (2.208 g)
customThis material was purified by chromatography on EM silica gel 60 (230-400 mesh, 115 mL dry)
washas eluting solvent

Sources & evidence

ORD record: ord-3dd93824a4984141a072324890d98328
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Linked notes

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