Isobutyraldehyde → Methyl 2-(isobutylamino)thiophene-3-carboxylate

HRID 1013876

반응식

HRID 1013876 반응식
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH:11](=O)[CH:12]([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[CH2:11]([NH:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])[CH:12]([CH3:14])[CH3:13]

참가 물질

6

반응물 3

HCID 6561IsobutyraldehydeHCID 78381Methyl 2-amino-3-thenoateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 67317044Methyl 2-(isobutylamino)thiophene-3-carboxylate

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 2-aminothiophene-3-carboxylate (2.0 g, 12.7 mmol) in dichloromethane (40 mL) and glacial acetic acid (0.72 mL) were added isobutyraldehyde (0.87 g, 12.1 mmol) and sodium triacetoxyborohydride (4.0 g, 18.9 mmol). The reaction mixture was stirred for 18 h at room temperature and concentrated. The residue was dissolved in ethyl acetate, washed with aqueous sodium bicarbonate solution and with water, dried over anhydrous sodium sulfate and concentrated. The residual oil was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate-hexane to afford the title compound as a slightly yellow oil (2.19 g, 81% % yield). 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 1H), 6.18 (d, 1H), 3.80 (s, 3H), 3.20 (m, 2H), 1.68 (m, 1H), 1.00 (d, 6H).

후처리

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate solution and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residual oil was purified on a silica gel flash chromatography column
  7. washeluted with 5% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-cd5b1c4c830448adbed656dbdebc96a4
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07982040B2

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