Potassium Carbonate → HCID 89477977, compound

HRID 1483192Notes

Reaction equation

HRID 1483192 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[C:20]#[CH:21]>O1CCCC1>[C:24]([O:23][C:19](=[O:22])[C:20]#[C:21][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 69258Methyl 3-iodobenzoateHCID 543038tert-Butyl propiolate

Product 1

HCID 89477977HCID 89477977, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To the mixture of methyl 3-iodobenzoate (157 mg, 0.60 mmol), potassium carbonate (166 mg, 1.20 mmol), cupper(I) iodide (14 mg, 0.07 mmol) and PdCl2(Ph3P)2 (21 mg, 0.03 mmol) in tetrahydrofuran (2 mL) was added tert-butyl propiolate (330 μL, 2.40 mmol) at room temperature. After stirred for 20 h at 60° C., the mixture was evaporated to dryness. The residue was chromatographed on a silica gel (EtOAc:hexanes=0:1˜1:10) to give the title compound 9-1 (155 mg, 99% yield) as a light brown oil.

Workup

  1. customthe mixture was evaporated to dryness
  2. customThe residue was chromatographed on a silica gel (EtOAc:hexanes=0:1˜1:10)

Sources & evidence

ORD record
ord-de4252b056e64d338542ff0bc705de82
Source dataset
uspto-grants-2016_08
Patent number
US09416121B2

Reaction notes

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