Water → HCID 58575556, compound

HRID 1189469Notes

Reaction equation

HRID 1189469 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=[O:29].O.[O:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1>C(OCC)(=O)C>[C:46]([O:45][CH2:49][CH2:48][O:12][C:4]1[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=[O:29])[CH3:47]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 58575556HCID 58575556, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2 g of methyl 4-fluoro-2-hydroxybenzoate in 60 mL of tetrahydrofuran were added 1.83 g of hydroxyethyl 2-acetate and 3.56 g of tributylphosphine, and then 5.93 g of 1,1′-(azodicarbonyl)dipiperidine was slowly added thereto under ice-cooling, followed by stirring for 20 minutes. The mixture was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into a mixed liquid of water and ethyl acetate. The aqueous layer was separated, the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 2.4 g of methyl 2-(2-acetoxyethoxy)-4-fluorobenzoate.

Workup

  1. temperatureunder ice-cooling
  2. stirringstirred for 6 hours
  3. customThe aqueous layer was separated
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0008cf0559a44d2ea39f3dddaad93da5
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

Loading…