Potassium Carbonate → 1-Ethynyl-4-(1-methoxycyclopropyl)-benzene

HRID 1935844Notes

Reaction equation

HRID 1935844 reaction equation
[CH3:1][O:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]#[C:13][Si](C)(C)C)=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:3]2([O:2][CH3:1])[CH2:4][CH2:5]2)=[CH:7][CH:8]=1)#[CH:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22568890[4-(1-Methoxycyclopropyl)phenylethynyl]-trimethylsilane2×

Product 1

HCID 225689501-Ethynyl-4-(1-methoxycyclopropyl)-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure E; [4-(1-methoxycyclopropyl)-phenylethynyl]-trimethylsilane (Intermediate 60, 285.0 mg, 1.18 mmols) in methanol (10 mL) was treated with potassium carbonate (100.0 mg, 0.72 mmol) and stirred overnight at ambient temperature. The crude alkyne (220 mg, 100%) was used directly in the next reaction. 1H NMR (CDCl3) δ: 7.46 (2H, d, J=8.2 Hz), 7.24 (2H, d, J=8.2 Hz), 3.23 (3H, s), 3.06 (1H, s), 1.22 (2H, m), 0.98 (2H, m).

Sources & evidence

ORD record
ord-192b25b855c24db081d2c385407ff3fb
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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