Hydrochloric Acid → 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one

HRID 1881847Notes

Reaction equation

HRID 1881847 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:14](N(OC)C)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:27]([Mg]Br)=[CH:28][CH3:29].Cl>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14](=[O:15])[CH:27]=[CH:28][CH3:29])[CH2:20][CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 593315972-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178456053HCID 178456053, compound

Product 1

HCID 684311882-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (1.00 g) in tetrahydrofuran (10 mL) was added 1-propenylmagnesium bromide (0.5M tetrahydrofuran solution, 17.2 mL) under ice-cooling, and the mixture was warmed to room temperature and stirred for 3 hr. The reaction mixture was poured into a mixture of concentrated hydrochloric acid (5 mL) and ice (100 g), and the mixture was stirred for 15 min. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (632 mg, yield 61%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 363 (MH+).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 min
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-717b76213c154864bbedb746a43fbb45
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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