Hydrochloric Acid → 2-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

HRID 1453627Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]([O:21]CC)=[CH2:20])CCC.Cl>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:19](=[O:21])[CH3:20])[CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 15, 1.20 g, 5.94 mmol) in 20 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (4.29 g, 11.88 mmol) and PdCl2(PPh3)2 (422 mg, 0.60 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, then extracted 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 (669 mg, 56% yield) as a colorless oil:

Workup

customby bubbling with argon for 30 min
temperaturethe mixture was cooled to room temperature
stirringThe mixture was then stirred for another 30 min
extractionextracted with ethyl acetate (3×10 mL)
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-b532222ba5e2412ab94f1e8be79c8652
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476673B2

Reaction notes

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