Epibromohydrin → HCID 86702130, compound

HRID 1776181Notes

Reaction equation

HRID 1776181 reaction equation
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH2:14]([CH:16]1[O:18][CH2:17]1)Br>CN(C)C=O.C(OCC)(=O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][N:9]([CH2:14][CH:16]1[CH2:17][O:18]1)[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 240162N-[(Furan-2-yl)methyl]methanesulfonamide

Product 1

HCID 86702130HCID 86702130, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% mineral oil dispersion, 0.524 g, 13.1 mmol) was added in portions to a 0° C. solution of N-(furan-2-ylmethyl)methanesulfonamide (2.0 g, 11.4 mmol) in 38 ml anhydrous N,N-dimethylformamide (38 mL), and the resultant mixture was allowed to warm to room temperature and stirred for 1 hour. Epibromohydrin (1.2 mL, 14.3 mmol) was added slowly, and the reaction was stirred for 3 hours at room temperature and 16 hours at 70° C. The reaction was cooled, diluted with ethyl acetate, and successively washed twice with water and once with saturated aqueous sodium chloride solutions. The organic layer was dried (anhydrous sodium sulfate), filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (25-60% ethyl acetate in hexanes) to give a pale yellow liquid (2.2 g, 84%). 1H NMR (CDCl3, 300 MHz) δ 7.40-7.39 (m, 1H), 6.37-6.35 (m, 2H), 4.64-4.50 (br dd, 2H, J=25.8, 16.5 Hz), 3.61-3.55 (m, 1H), 3.22-3.12 (m, 2H), 2.82 (s, 3H), 2.82-2.79 (m, 1H), 2.62-2.60 (m, 1H). ESI (m/z): 232.0 (M+H).

Workup

  1. stirringthe reaction was stirred for 3 hours at room temperature and 16 hours at 70° C
  2. temperatureThe reaction was cooled
  3. washsuccessively washed twice with water and once with saturated aqueous sodium chloride solutions
  4. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by silica gel column chromatography (25-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-287c02e7c51042d2b6cfda742c026a2a
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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