1-Bromo-2-methylpropane → HCID 86702131、化合物

HRID 1776182ノート

反応式

HRID 1776182 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].Br[CH2:15][CH:16]([CH3:18])[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][N:9]([CH2:17][C:16]([CH3:18])=[CH2:15])[S:10]([CH3:13])(=[O:12])=[O:11]

参加物

6

反応物 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 240162N-(furan-2-ylmethyl)methanesulfonamide

生成物 1

HCID 86702131HCID 86702131、化合物収率 95%

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, 0.284 g, 7.1 mmol) was added in portions to a stirring solution of N-(furan-2-ylmethyl)methanesulfonamide (1.0 g, 5.7 mmol) in anhydrous N,N-dimethylformamide (12 mL), which was kept at 0° C. by an external ice bath. The ice bath was removed and the mixture was stirred for 50 mins at ambient temperature. 3-bromo-2-methylpropane (1.15 g, 8.6 mmol) was added in one portion, and the resulting mixture was stirred overnight at 65° C. before being diluted with ethyl acetate. The organic layer was successively washed with water and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), filtered, and concentrated. The crude material was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to give a clear liquid (1.24 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.41-7.40 (m, 1H), 6.38-6.34 (m, 1H), 6.29-6.28 (m, 1H), 5.03-5.00 (m, 2H), 4.37 (s, 2H), 3.73 (s, 2H), 2.76 (s, 3H), 1.77 (s, 3H).

後処理

  1. customwas kept at 0° C. by an external ice bath
  2. customThe ice bath was removed
  3. stirringthe resulting mixture was stirred overnight at 65° C.
  4. washThe organic layer was successively washed with water and saturated aqueous sodium chloride solutions
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-1c0706801581426885fdc06e0a90edc4
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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