Methyl propionate → HCID 89526456, compound

HRID 1523303Notes

Reaction equation

HRID 1523303 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][CH3:3].[Li+].CC([N-]C(C)C)C.[CH3:15][C:16]([S:19]([N:21]=[C:22]1[CH2:25][O:24][CH2:23]1)=[O:20])([CH3:18])[CH3:17]>C1COCC1>[C:16]([S:19]([NH:21][C:22]1([CH:2]([CH3:3])[C:1]([O:5][CH3:6])=[O:4])[CH2:25][O:24][CH2:23]1)=[O:20])([CH3:15])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 11124Methyl propionateHCID 2724682Lithium diisopropylamideHCID 468399952-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

Product 1

HCID 89526456HCID 89526456, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Methyl propionate (2.71 g, 30.8 mmol) was dissolved in anhydrous THF (90 mL) and cooled to −78° C. under nitrogen. LDA (2M solution in THF, 15 mL, 30 mmol) was added drop-wise. After 1 hour at −78° C., a solution of 2-methyl-N-oxetan-3-ylidenepropane-2-sulfinamide (Preparation 39, 1.35 g, 7.703 mmol) in anhydrous THF (10 mL) was added. The reaction was gradually warmed to room temperature and stirred for 18 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound as an oil (1.276 g, 63% yield).

Workup

  1. temperatureThe reaction was gradually warmed to room temperature
  2. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-708eb3b75b1a480ea837600e26c300d4
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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