Potassium Carbonate → HCID 86627697, compound

HRID 2241005Notes

Reaction equation

HRID 2241005 reaction equation
[F:1][CH:2]([F:18])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[C:13][Si](C)(C)C)[CH:9]=[CH:10][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CO.O.CCOC(C)=O>[F:1][CH:2]([F:18])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[CH:13])[CH:7]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 67536959HCID 67536959, compound

Product 1

HCID 86627697HCID 86627697, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ((3-(3,3-difluoropropoxy)phenyl)ethynyl)trimethylsilane (2.1 g, 7.82 mmol) from the previous step in MeOH (19.5 mL) was added K2CO3 (10.81 g, 78.2 mmol) at room temperature. The reaction mixture was stirred for 1.5 h after which it was diluted with water and EtOAc. The aqueous layer was separated and extracted with EtOAc once. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give a brown oil. The oil was absorbed onto Celite (8 g). Flash chromatography (SiO2, 1% EtOAc 99% Hexanes to 3% EtOAc 97% Hexanes) provided 1.31 g, 85%, of the title compound as a yellow oil.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc once
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customThe oil was absorbed onto Celite (8 g)
  8. customFlash chromatography (SiO2, 1% EtOAc 99% Hexanes to 3% EtOAc 97% Hexanes) provided 1.31 g, 85%

Sources & evidence

ORD record
ord-6f8f061dbc56444592821ee2a0f982f2
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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