Potassium Carbonate → HCID 86627700, compound

HRID 2241008Notes

Reaction equation

HRID 2241008 reaction equation
[F:1][CH:2]([F:19])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:13]#[C:14][Si](C)(C)C)[CH:9]=[CH:10][C:11]=1[F:12].C([O-])([O-])=O.[K+].[K+]>CO>[F:19][CH:2]([F:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:13]#[CH:14])[CH:9]=[CH:10][C:11]=1[F:12]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67536451HCID 67536451, compound

Product 1

HCID 86627700HCID 86627700, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the crude ((3-(3,3-difluoropropoxy)-4-fluorophenyl)ethynyl)trimethylsilane (2.0 g) from the previous step in MeOH (17.5 mL) was added K2CO3 (9.65 g, 69.8 mmol) at room temperature. The reaction mixture was stirred for 1.5 h after which the mixture was filtered. The filter cake was washed with MeOH and the combined filtrate was concentrated over 10 g Celite. Flash chromatography (SiO2, % EtOAc 99% Hexanes to 5:95 EtOAc:Hexanes) provided 700 mg, 76%, of the title compound as a light yellow oil.

Workup

  1. filtrationwas filtered
  2. washThe filter cake was washed with MeOH
  3. concentrationthe combined filtrate was concentrated over 10 g Celite
  4. customFlash chromatography (SiO2, % EtOAc 99% Hexanes to 5:95 EtOAc:Hexanes) provided 700 mg, 76%

Sources & evidence

ORD record
ord-46516f2f97c24d47a2a4d440e64101b5
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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