Methanol → 8-Cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone

HRID 1765871Notes

Reaction equation

HRID 1765871 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]#[C:18][Si](C)(C)C)[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3([CH3:16])[CH3:15])[CH2:3][CH2:2]1.CO.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CCCCCC>[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]#[CH:18])[CH:7]=[C:8]3[C:13]=2[C:12](=[O:14])[CH2:11][CH2:10][C:9]3([CH3:15])[CH3:16])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 211072428-Cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone2×

Product 1

HCID 211072418-Cyclopropyl-4,4-dimethyl-6-ethynyl-1-tetralone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following General Procedure F and using 8-cyclopropyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-1-tetralone (Intermediate 159, 1.05 g, 3.38 mmol), methanol (20 mL) and potassium carbonate (1 g, 14.5 mmol) followed by flash column chromatography using 7% ethyl acetate in hexane as the eluent, the title compound was obtained (0.57 g, 80%) as a pale yellow solid.

Sources & evidence

ORD record
ord-2b9536123c0942b1818193a6ba7ff153
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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