Potassium Carbonate → 1-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene

HRID 395129Notes

Reaction equation

HRID 395129 reaction equation
[CH2:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][Si](C)(C)C)=[CH:14][C:13]=2[CH2:24][CH3:25])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:10]2)=[C:13]([CH2:24][CH3:25])[CH:14]=1)#[CH:19]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22568833[4-(1-Benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-trimethylsilane2×

Product 1

HCID 225689831-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure E; [4-(1-benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-trimethylsilane (Intermediate 89, 240 mg, 0.69 mmol) in methanol (6 mL) was treated with potassium carbonate (10.0 mg, 0.72 mmol) and stirred overnight at ambient temperature. The crude alkyne (190 mg, 99%) was used directly in the next reaction. 1H NMR (CDCl3) δ: 7.43-7.15 (8H, m), 4.27 (2H, s), 3.08 (1H, s), 3.01 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz), 1.22 (2H, m), 0.92 (2H, m).

Sources & evidence

ORD record
ord-a6fffd791039464fb31dfd06886b9df9
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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