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

HRID 51724Notes

Reaction equation

HRID 51724 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-eb375b016b924335b10fe63e2ecfb622
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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