Potassium Carbonate → 4-Ethynyl-1-(1-benzyloxycyclopropyl)-2-methyl-benzene

HRID 841408Notes

Reaction equation

HRID 841408 reaction equation
[CH2:1]([O:8][C:9]1([C:12]2[CH:17]=[CH:16]C(C#CC3C=CC(C(OCC)=O)=CC=3)=C[CH:13]=2)[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:3]([C:2]1[CH:7]=[CH:13][C:12]([C:9]2([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:10][CH2:11]2)=[C:17]([CH3:16])[CH:1]=1)#[CH:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22568905Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate2×

Product 1

HCID 225688524-Ethynyl-1-(1-benzyloxycyclopropyl)-2-methyl-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure E; [4-(1-benzyloxycyclopropyl)-3-methyl-phenylethynyl]-trimethylsilane (Intermediate 75, 300.0 mg, 0.95 mmols) in methanol (6 mL) was treated with potassium carbonate (120.0 mg, 0.87 mmol) and stirred overnight at ambient temperature. The crude alkyne (185 mg, 79%) was used directly in the next reaction.

Sources & evidence

ORD record
ord-4ea296d84dd3498f92a23e8e91032487
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

Loading…