Morpholine → 3-Propyl-tetrahydrothiopyran-4-one

HRID 1638141Notes

Reaction equation

HRID 1638141 reaction equation
[CH2:1]([C:4]1(C(O)=O)[C:9](=[O:10])[CH2:8][CH2:7][S:6][CH2:5]1)[CH2:2][CH3:3].N1CCOCC1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([CH:4]1[C:9](=[O:10])[CH2:8][CH2:7][S:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 226177553-Propyl-tetrahydrothiopyran-4-one-3-carboxylic acid

Product 1

HCID 110409693-Propyl-tetrahydrothiopyran-4-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-propyl-tetrahydrothiopyran-4-one-3-carboxylic acid, allyl ester (0.272 g, 1.1 mmol) in 5.0 mL dry tetrahydrofuran at room temperature was successively added morpholine (0.979 g, 1.12 mmol) followed by tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.055 mmol). Stirring was continued until the thin layer chromatography indicated the completion of reaction at which point the reaction mixture was evaporated and the crude product was purified by flash column chromatography on silica gel eluted eluted with hexane:ether (19:1) to give 0.163 g of 3-propyl-tetrahydrothiopyran-4-one.

Workup

  1. customat room temperature
  2. customthe completion of reaction at which
  3. customwas evaporated
  4. customthe crude product was purified by flash column chromatography on silica gel
  5. washeluted
  6. washeluted with hexane:ether (19:1)

Sources & evidence

ORD record
ord-786a4e35ff2b4169afd82d2ab0f2310d
Source dataset
uspto-grants-2000_03
Patent number
US06043358

Reaction notes

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