Methanol → 8-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]

HRID 841614Notes

Reaction equation

HRID 841614 reaction equation
[CH:1]1([C:4]2[C:15]3[O:14][C:11]4([CH2:13][CH2:12]4)[CH2:10][C:9]([CH3:17])([CH3:16])[C:8]=3[CH:7]=[C:6]([C:18]#[C:19][Si](C)(C)C)[CH:5]=2)[CH2:3][CH2:2]1.CO.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CCCCCC>[CH:1]1([C:4]2[C:15]3[O:14][C:11]4([CH2:13][CH2:12]4)[CH2:10][C:9]([CH3:16])([CH3:17])[C:8]=3[CH:7]=[C:6]([C:18]#[CH:19])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 225688398-Cyclopropyl-3,4-dihydro-4,4-dimethyl-6-(trimethylsilanyl)ethynylspiro[2 H 1-benzopyran-2,1'-cyclopropane]2×

Product 1

HCID 225689518-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following general procedure E, and 8-cyclopropyl-3,4-dihydro-4,4-dimethyl-6-(trimethylsilanyl)ethynylspiro[2H-1-benzopyran-2,1′-cyclopropane] (Intermediate 43, 0.62 g, 1.9 mmol), methanol and potassium carbonate (0.5 g, 3.6 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 1-2% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.5 g, 100%).

Sources & evidence

ORD record
ord-21f1832142204b2bbc95ead5625d819e
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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