Tetrabutylammonium Fluoride → HCID 57475885, compound

HRID 1941866Notes

Reaction equation

HRID 1941866 reaction equation
Cl[CH2:2][C:3]1[O:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1.[F-:12].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.O>[CH3:11][O:10][C:8]([C:6]1[N:7]=[C:3]([CH2:2][F:12])[O:4][CH:5]=1)=[O:9]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylate

Product 1

HCID 57475885HCID 57475885, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 2-(chloromethyl)oxazole-4-carboxylate (CAS208465-72-9) (150 mg, 0.85 mmol) in acetonitrile (4.27 ml) was treated with tetra-n-butylammonium fluoride (2.56 ml, 2.56 mmol). The blue solution turned to orange and was left under stirring at room temperature overnight. For the workup, the reaction mixture was poured in water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated at reduced pressure. The crude material was purified by chromatography on a flash NH2 column using a gradient of heptane/ethyl acetate=100/0 to 50/50 as the eluent. The 2-fluoromethyl-oxazole-4-carboxylic acid methyl ester was obtained as a white solid (64 mg, 47% of theory). MS (ISP): m/z=160.1 [M+H]+. b) 2-Fluoromethyl-oxazole-4-carboxylic acid

Workup

  1. waitwas left
  2. extractionextracted two times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated at reduced pressure
  6. customThe crude material was purified by chromatography on a flash NH2 column

Sources & evidence

ORD record
ord-36c701d6bd444d829d574b1dd89cd1ca
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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