Hydrochloric Acid → 3,4-Dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene

HRID 853192Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[CH:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:26]([O:28]CC)=[CH2:27])CCC.Cl.C(OCC)(=O)C>C1COCC1.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>[CH3:12][C:9]1([CH3:13])[C:10]2[CH:11]=[C:2]([C:26](=[O:28])[CH3:27])[CH:3]=[CH:4][C:5]=2[C:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:7][CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 7-bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydro-naphthalene (Compound 4, 295 mg, 0.90 mmol) in 5 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (650 mg, 1.80 mmol) and PdCl2(PPh3)2 (63 mg, 0.09 mmol) were added. After stirring at 80° C. for 18 h, the mixture was cooled to room temperature and 3 mL of 10% HCl was added. The mixture was then stirred for another 30 min before extraction with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (80:20 hexane/ethyl acetate) afforded the title compound (248 mg, 95% yield) as a colorless oil:

Workup

customby bubbling with argon for 30 min
temperaturethe mixture was cooled to room temperature
washThe combined organic layer was washed with brine (1×10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure
customPurification by flash chromatography (80:20 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-49eb2f6c3d384ff28598574b44ece3bd
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253319B2

Reaction notes

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