Hydrochloric Acid → HCID 59191306, compound

HRID 626011Notes

Reaction equation

HRID 626011 reaction equation
[F:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[O:17][CH3:18])[CH:5]=[CH:4][CH:3]=1.[F:19][C:20]([Si](C)(C)C)([F:22])[F:21].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1.C(OCC)C.O>[F:19][C:20]([F:22])([F:21])[CH:13]([C:12]1[CH:15]=[CH:16][C:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)=[C:10]([O:17][CH3:18])[CH:11]=1)[OH:14]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 24785927HCID 24785927, compound

Product 1

HCID 59191306HCID 59191306, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(6-fluoropyridin-2-yl)oxy]-3-methoxy benzaldehyde (300 mg; 1.2 mmol) with trifluoro methyltrimethylsilane (228 μl; 1.46 mmol) in THF (3 ml) under argon at 0° C. was added a molar solution of TBAF in THF (10 μl; 0.012 mmol). The reaction mixture was allowed to stir at rt for 2 h and a molar aqueous solution of HCl was added dropwise (2.5 ml; 2.5 mmol). The reaction mixture was stirred for another 2 h. water and diethylether were added. The aqueous phase was further extracted (2×EtOAc). Combined organic phases were dried over MgSO4, concentrated in vacuo to afford the title compound as a white solid (333 mg; 1.05 mmol; 88%).

Workup

  1. additionwere added
  2. extractionThe aqueous phase was further extracted (2×EtOAc)
  3. dry with materialCombined organic phases were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1cf3c4e4cb24912824d6ed338e0c39e
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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