1-Bromo-2-methylpropane → HCID 86702131, 화합물

HRID 1776182노트

반응식

HRID 1776182 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 86702131HCID 86702131, 화합물수율 95%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1c0706801581426885fdc06e0a90edc4
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265772B2

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