Hydrochloric Acid → 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

HRID 1881910Notes

Reaction equation

HRID 1881910 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:13](N(OC)C)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[CH:26]([Mg]Br)=[CH2:27].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:13](=[O:14])[CH:26]=[CH2:27])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 593313932-[3-chloro-4-(methylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178418507HCID 178418507, compound

Product 1

HCID 593312984-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[3-chloro-4-(methylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (8.64 g) in tetrahydrofuran (90 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 88.8 mL) was added dropwise. The reaction mixture was stirred at room temperature for 3 hr, and added to 1M hydrochloric acid, and the mixture was stirred for 30 min. The reaction 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 (7.15 g, yield 90%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ec3bc3ce3b0471a93008581ecbf6658
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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