Hydrochloric Acid → HCID 59331489, compound

HRID 1881936Notes

Reaction equation

HRID 1881936 reaction equation
CON(C)[C:4](=[O:22])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][O:8]1.[CH:24]([Mg]Br)=[CH2:25].Cl>O1CCCC1>[CH3:21][S:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][O:8]2)[C:4](=[O:22])[CH:24]=[CH2:25])=[CH:17][CH:16]=1)(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59331371HCID 59331371, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 59331489HCID 59331489, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methoxy-N-methyl-2-[4-(methylsulfonyl)phenyl]-3-(tetrahydrofuran-2-yl)propanamide (1.68 g) in tetrahydrofuran (19.7 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 19.7 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 3 hr, and poured into 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 (930 mg, yield 61%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 309 (MH+).

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-6429911123dd481e94c3717060ead9dd
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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