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

HRID 22930

反応式

HRID 22930 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-8e35362516b442d983fbea020c66b3ad
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

関連ノート

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