7-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one → 4,4-Dimethyl-7-ethynyl-1-tetralone

HRID 233097

Reaction equation

HRID 233097 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][C:6]2([CH3:15])[CH3:14])#C.Br[C:17]1C=C2C(C(C)(C)CCC2=O)=C[CH:18]=1>>[C:17]([C:12]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:15])[CH2:7][CH2:8][C:9]2=[O:13])=[CH:4][CH:3]=1)#[CH:18]

Participants

3

Reactant 2

HCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2×HCID 225688236-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one2×

Product 1

HCID 107504764,4-Dimethyl-7-ethynyl-1-tetralone

Procedure

Employing the same general procedure as for the preparation of 6-ethynyl-3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-one (Compound K), 7 g (27.6 mmol) of 7-bromo-3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-one (Compound G) was converted into the title compound using 39 ml (36.6 mmol) of trimethylsilyl acetylene, 0.97 g (1.3 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.26 g (1.3 mmol) of cuprous iodide and 0.6 g (4.3 mmol) of K2CO3.

Sources & evidence

ORD record
ord-66fe203aeb96490c9e32fdf6a2e6fbe0
Source dataset
uspto-grants-1997_01
Patent number
US05591858

Linked notes

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