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

HRID 2299419Notes

Reaction equation

HRID 2299419 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-73e2879b66164707ac44266bc7d4c257
Source dataset
uspto-grants-2002_12
Patent number
US06495552B2

Reaction notes

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