Iodoethane → tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamate

HRID 17171

反応式

HRID 17171 の反応式
[H-].[Na+].[CH2:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]#[CH:5].[CH2:14](I)[CH3:15]>CN(C=O)C.O>[CH2:14]([N:6]([CH2:3][C:4]#[CH:5])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH3:15]

参加物

6

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

生成物 1

HCID 18366151tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamate収率 47%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A suspension of sodium hydride (354 mg, 14.2 mmol) in DMF (33 mL) at room temperature was treated with a solution of Example 516A (2.0 g, 12.9 mmol) in DMF (10 mL) and stirred for one hour at room temperature. The solution was cooled to 0° C., treated with ethyl iodide (1.24 mL, 15.5 mmol), stirred for one hour at 0° and overnight at room temperature. The solution was diluted with water (25 mL), extracted with diethyl ether (2×50 mL) and the combined organic layers were washed with brine (30 mL0, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using 5-10% ethyl acetate/hexanes to give the 1.1 g (47% yield) of the desired product. MS (ESI(+)) m/e 184 (M+H)+.

後処理

  1. temperatureThe solution was cooled to 0° C.
  2. stirringstirred for one hour at 0° and overnight at room temperature
  3. extractionextracted with diethyl ether (2×50 mL)
  4. washthe combined organic layers were washed with brine (30 mL0
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel using 5-10% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-093ae3d4bbe64e2187e00394a517fbec
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

関連ノート

読み込み中…