1-(Tetrahydro-2H-pyran-4-yl)ethanone → HCID 88859379, compound

HRID 2206636Notes

Reaction equation

HRID 2206636 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7](=O)[CH3:8])[CH2:3][CH2:2]1.[CH3:10][C:11]([S@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>O1CCCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH3:10][C:11]([S@:14](/[N:16]=[C:7](/[CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)\[CH3:8])=[O:15])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 98773651-(Tetrahydro-2H-pyran-4-yl)ethanoneHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 88859379HCID 88859379, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (1.9 g, 14.8 mmol) in tetrahydrofuran (30 mL) was added (R)-2-methylpropane-2-sulfinamide (2.15 g, 17.8 mmol) and tetraethoxytitanium (5.06 g, 22.2 mmol) at 25° C. under N2. The reaction was refluxed for 7 hrs. Then the mixture was quenched by water, extracted with ethyl acetate and filtered. The crude product was purified by column chromatography on silica gel eluted with dichloromethane: methanol=200:1 to give (R,E)-2-methyl-N-(1-(tetrahydro-2H-pyran-4-yl)ethylidene)propane-2-sulfinamide (1.5 g, 44.1%) as a yellow oil.

Workup

  1. temperatureThe reaction was refluxed for 7 hrs
  2. customThen the mixture was quenched by water
  3. extractionextracted with ethyl acetate
  4. filtrationfiltered
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluted with dichloromethane

Sources & evidence

ORD record
ord-7174b65a31a74bb9883b282ea6843292
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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