Epibromohydrin → HCID 86702130、化合物

HRID 1776181ノート

反応式

HRID 1776181 の反応式
[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]

参加物

6

反応物 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 240162N-(furan-2-ylmethyl)methanesulfonamide

生成物 1

HCID 86702130HCID 86702130、化合物収率 84%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-287c02e7c51042d2b6cfda742c026a2a
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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