HCID 11255392, compound → Benzyl 2-[(pyridin-4-yl)oxy]propanoate

HRID 1160699Notes

Reaction equation

HRID 1160699 reaction equation
C[Si](CCOC[N:9]1[CH:14]=[CH:13][C:12](=[O:15])[CH:11]=[CH:10]1)(C)C.FC(F)(F)S(O[CH:22]([CH3:33])[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])(=O)=O>C(Cl)Cl>[N:9]1[CH:10]=[CH:11][C:12]([O:15][CH:22]([CH3:33])[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11255392HCID 11255392, compoundHCID 140051601-{[2-(Trimethylsilyl)ethoxy]methyl}pyridin-4(1H)-one

Product 1

HCID 16098332Benzyl 2-[(pyridin-4-yl)oxy]propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of benzyl lactate (6.0 g, 33 mmol) and N-methyl morpholine (2.7 mL, 33 mmol) in 100 mL anhydrous CH2Cl2 at −20° C. was added trifluoromethanesulfonyl anhydride (5.6 mL, 33 mmol). After stirring at −20° C. for 1 h, the reaction mixture was diluted with 100 mL hexane and washed with dilue aqueous sodium hydrogen sulfate and brine/saturated aqueous sodium bicarbonate. The organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluted with 10% ether in hexane to give benzyl 2-trifluoromethanesulfonyloxypropionate (6.4 g), which was used immediately for the ensuing reaction. Thus, a mixture of N-trimethylsilylethoxymethyl-4-pyridone (Step A, 3.4 g, 15 mmol) and benzyl 2-trifluoromethanesulfonyloxypropionate (4.7 g, 15 mmol) was heated at 60° C. overnight. After cooling to room temperature, the reaction mixture was dissolved in CH2Cl2 and loaded onto a silica gel column, which was eluted with 5% MeOH in CH2Cl2 to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.57 (d, 2H), 7.42 (d, 2H), 7.4-7.3 (m, 5H), 5.44 (q, 1H), 5.24 (ABq, 2H), 1.72 (d, 3H). LC-MS: m/e 258 (M+H)+ (1.8 min).

Workup

  1. customwas used immediately for the ensuing reaction
  2. temperatureAfter cooling to room temperature
  3. washwas eluted with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e7a9d67a097d49bd808c5a58040f46a4
Source dataset
uspto-grants-2010_10
Patent number
US07816534B2

Reaction notes

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