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

HRID 1270895

반응식

HRID 1270895 반응식
[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.C(OCC)C>[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-32b9a24309db4d56bd758a8eab83c705
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202363B2

연결된 노트

불러오는 중…