Acetic Acid → Methyl-(2E)-2-cyano-3-(2,3-dihydro-1-benzofuran-5-yl)-2-butenoate

HRID 22930

반응식

HRID 22930 반응식
[C:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][CH2:10][C:6]=2[CH:5]=1)(=O)[CH3:2].[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])#[N:14].C(N)C1C=CC=CC=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:19][O:18][C:16](=[O:17])/[C:15](/[C:13]#[N:14])=[C:1](/[C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][CH2:10][C:6]=2[CH:5]=1)\[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 7747Methyl cyanoacetateHCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanone

생성물 1

HCID 69746774Methyl-(2E)-2-cyano-3-(2,3-dihydro-1-benzofuran-5-yl)-2-butenoate수율 60.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a stirred solution of 5-acetyl-2,3-dihydrobenzo[b]furan (Aldrich) (1 g, 6.17 mmol) in toluene (60 ml) was added methyl cyanoacetate (0.60 ml, 6.78 mmol), benzylamine (0.07 ml, 0.61 mmol) and acetic acid (0.3 ml, 5.3 mmol) and the whole refluxed in a Dean-Stark apparatus for 16 h. The reaction mixture was cooled, washed with 2N HCl (30 ml), NaHCO3 (30 ml), brine (30 ml), dried (MgSO4) and evaporated to a yellow residue. This residue was purified by column chromatography using 15-20% EtOAc in pentane as eluant to provide the title product (902 mg, 60%); 1HNMR (400 MHz, CDCl3) δ: 2.65 (s, 3H), 3.25 (t, 2H), 3.9 (s, 3H), 4.6 (t, 2H), 6.8 (d, 1H), 7.25 (d, 1H), 7.8 (s, 1H); LRMS: M+NH4+, 261. (ES+).

후처리

  1. temperaturethe whole refluxed in a Dean-Stark apparatus for 16 h
  2. temperatureThe reaction mixture was cooled
  3. washwashed with 2N HCl (30 ml), NaHCO3 (30 ml), brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a yellow residue
  6. customThis residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-8e35362516b442d983fbea020c66b3ad
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849649B2

연결된 노트

불러오는 중…