Hydrochloric Acid → HCID 59331469, compound

HRID 1881845Notes

Reaction equation

HRID 1881845 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](/[C:13](=[CH: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)=[CH2:28].Cl>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[C:14](=[O:15])[CH:27]=[CH2:28])=[CH:20]\[CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59331445HCID 59331445, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 59331469HCID 59331469, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 mL) of (2E)-2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propan-2-enamide (1.13 g) in tetrahydrofuran was added vinylmagnesium bromide (1.0M tetrahydrofuran solution, 9 mL) under ice-cooling, and the mixture was warmed to room temperature and stirred overnight. An excess amount of 1M hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. 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 (426 mg, yield 41%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 347 (MH+).

Workup

  1. temperaturecooling
  2. extractionthe 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-0dff29a3c11b4f04b9c84ced8ac6aa9b
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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