Potassium Carbonate → 8-Ethyl-6-ethynyl-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 1870023Notes

Reaction equation

HRID 1870023 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:16]#[C:17][Si](C)(C)C)[CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][C:8]2([CH3:15])[CH3:14])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([C:3]1[CH:4]=[C:5]([C:16]#[CH:17])[CH:6]=[C:7]2[C:12]=1[C:11](=[O:13])[CH2:10][CH2:9][C:8]2([CH3:14])[CH3:15])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 211072528-Ethyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-3,4-dihydro-2H-naphthalen-1-one2×

Product 1

HCID 211072538-Ethyl-6-ethynyl-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following General Procedure F and using 8-ethyl-4,4-dimethyl-6-(trimethylsilanyl)ethynyl-3,4-dihydro-2H-naphthalen-1-one (Intermediate 179, 0.66 g, 2.2 mmol), methanol (10 mL) and potassium carbonate (0.4 g, 2.9 mmol) the title compound was obtained as an orange oil (0.59 g, 100%). 1H NMR (300 MHz, CDCl3): δ 7.51 (d, 1H, J=1.51 Hz), 7.37 (d, 1H, J=1.5 Hz), 3.32 (s, 1H), 3.10 (q, 2H, J=7.3 Hz), 2.84 (t, 2H, J=6.7 Hz), 2.08 (t, 2H, J=6.7 Hz), 1.48 (s, 6H), 1.33 (t, 3H, J=7.3 Hz).

Sources & evidence

ORD record
ord-ffce7bba749141ee81e0cf0f1bac391b
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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