Hexane → 6-Bromo-8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]

HRID 51681Notes

Reaction equation

HRID 51681 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH2:17])[C:5]2[O:12][C:9]3([CH2:11][CH2:10]3)[CH2:8][C:7]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.[N+](=[CH2:20])=[N-].CCCCCC>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]2[CH2:20][CH2:17]2)[C:5]2[O:12][C:9]3([CH2:10][CH2:11]3)[CH2:8][C:7]([CH3:13])([CH3:14])[C:6]=2[CH:15]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 9550DiazomethaneHCID 225688556-Bromo-3 4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1'-cyclopropane]2×

Product 1

HCID 225689116-Bromo-8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

Following general procedure O and, using A 6-bromo-3,4-dihydro-4,4-dimethyl-8-vinylspiro[2H-1-benzopyran-2,1′-cyclopropane] (Intermediate 41, 1.36 g, 4.6 mmol), a solution of diazomethane in diethyl ether and palladium(II)acetate (˜30 mg) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as the eluent, the title compound was obtained as a clear oil (1.38 g, 100%).

Sources & evidence

ORD record
ord-3ce0bcf5b56e42478c2fc066a25430db
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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