Phenol → Phenyl oxane-4-carboxylate

HRID 2076917Notes

Reaction equation

HRID 2076917 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[C:10]1(O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 996PhenolHCID 8471TriethylamineHCID 219302Oxane-4-carboxylic acidHCID 2724699PyBOP

Product 1

HCID 23131607Phenyl oxane-4-carboxylateYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Tetrahydropyran-4-carboxylic acid (1.00 g, 7.69 mmol), phenol (651 mg, 6.92 mmol), and PyBOP (4.40 g, 8.45 mmol) were dissolved in DMF (15 mL). To the solution was added triethylamine (2.36 mL, 16.9 mmol), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with saturated sodium bicarbonate aqueous solution and brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give phenyl tetrahydropyran-4-carboxylate (1.28 g, 81%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-1256cf56610145ab809ddc3e8d907564
Source dataset
uspto-grants-2011_04
Patent number
US07928098B2

Reaction notes

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