Tetrahydrofuran → HCID 117992043, compound

HRID 589012Notes

Reaction equation

HRID 589012 reaction equation
CC(C)([O-])C.[K+].C1COCC1.[CH3:12][O:13][C:14](=[O:35])[CH2:15][O:16][CH:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:18][C:19]1[C:20]([C:25](OC)=[O:26])=[N:21][CH:22]=[CH:23][CH:24]=1>C1(C)C(C)=CC=CC=1>[OH:26][C:25]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH2:18][CH:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:16][C:15]=1[C:14]([O:13][CH3:12])=[O:35]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 90013475HCID 90013475, compound

Product 1

HCID 117992043HCID 117992043, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
82 °C

Procedure

A solution of potassium tert-butoxide in THF (1M, 10 mL, 10 mmol), was added dropwise to a solution of methyl 3-(2-(2-methoxy-2-oxoethoxy)-2-phenylethyl)picolinate (3.0 g, 9.1 mmol) in xylene (20 mL) at 28° C. The resulting mixture was heated at 82° C. for 2 h, then cooled and concentrated. The residue was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether to give the title compound. MS: m/z=298.2 (M+1).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-992f8c13d596450c81f2c6ef63a8a543
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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