Tributylphosphine → HCID 66696256, compound

HRID 1396664Notes

Reaction equation

HRID 1396664 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.[O:13]1[CH2:17][CH2:16][CH:15]([CH2:18]O)[CH2:14]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)(=O)C.O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:18][CH:15]2[CH2:16][CH2:17][O:13][CH2:14]2)[CH:3]=1

Participants

8

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 139980Tetrahydro-3-furanmethanolHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 66696256HCID 66696256, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3 g of methyl 4-fluoro-2-hydroxybenzoate in 60 mL of tetrahydrofuran were added 1.98 g of tetrahydrofuran-3-ylmethanol and 4.28 g of tributylphosphine, followed by ice-cooling. To a mixture was gradually added 6.67 g of 1,1′-(azodicarbonyl)dipiperidine, followed by stirring for 20 minutes. The mixture was warmed to room temperature, stirred for 16 hours, and then poured into a mixture 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 (n-hexane/ethyl acetate) to obtain 3.14 g of methyl 4-fluoro-2-(tetrahydrofuran-3-ylmethoxy)benzoate.

Workup

  1. temperaturecooling
  2. stirringstirred for 16 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 (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-96a967d31ef04a72a2cb2983509ea9ad
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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