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

HRID 1936082Notes

Reaction equation

HRID 1936082 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-3bc6e2c2d12f43d7b40624e628efe5df
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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