Hydrochloric Acid → Ethyl 2-(4-cyano-2-methoxyphenyl)-3-(dimethylamino)acrylate

HRID 526432ノート

反応式

HRID 526432 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][C:13]([CH3:16])(C)C)=[O:11])=[C:5]([O:17][CH3:18])[CH:4]=1)#[N:2].Cl.O1CCOCC1.C(C1C=CC(CC(OCC)=O)=C(OC)C=1)#N.C(O[CH:45](OCC)[N:46]([CH3:48])[CH3:47])C>C(O)C.CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH:45][N:46]([CH3:48])[CH3:47])[C:10]([O:12][CH2:13][CH3:16])=[O:11])=[C:5]([O:17][CH3:18])[CH:4]=1)#[N:2]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 70913Dimethylformamide diethylacetalHCID 117600541Ethyl 2-(4-cyano-2-methoxyphenyl)acetateHCID 117601441Tert-butyl 2-(4-cyano-2 methoxyphenyl)acetate

生成物 1

HCID 117601030Ethyl 2-(4-cyano-2-methoxyphenyl)-3-(dimethylamino)acrylate収率 74%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Combined tert-butyl 2-(4-cyano-2-methoxyphenyl)acetate (549 mg, 2.218 mmol) and 4N HCl in dioxane (0.277 mL, 1.109 mmol) in ethanol (7.4 mL) and stirred for 16 hours at 60° C. The reaction was concentrated by rotary evaporation and then combined with ethyl 2-(4-cyano-2-methoxyphenyl)acetate (0.486 g, 2.217 mmol) and 1,1-diethoxy-N,N-dimethylmethanamine (1.9 mL, 11.08 mmol) in DMF (4.43 mL) and stirred for 16 hours at 100° C. The reaction mixture was diluted with 200 mL EtOAc and washed twice with 200 mL water. Organic layer was dried with sodium sulfate and concentrated to give a residue which was purified on a 60 g NH silica gel column eluting with hexanes and EtOAc to give the title compound (405 mg, 74%).

後処理

  1. concentrationThe reaction was concentrated by rotary evaporation
  2. washwashed twice with 200 mL water
  3. dry with materialOrganic layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified on a 60 g NH silica gel column
  7. washeluting with hexanes and EtOAc

出典と根拠

ORDレコード
ord-8e16190dd5b04168948c0b4c0bd1e4ca
出典データセット
uspto-grants-2016_05
特許番号
US09345713B2

反応ノート

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