Potassium Carbonate → Methyl 6-(2-morpholinoethoxy)benzofuran-2-carboxylate

HRID 252855

反応式

HRID 252855 の反応式
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[CH:3]=1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CC(C)=O>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][O:1][C:2]2[CH:14]=[CH:13][C:5]3[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=3[CH:3]=2)[CH2:19][CH2:20]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 12082972Methyl 6-hydroxy-1-benzofuran-2-carboxylate

生成物 1

HCID 59736920Methyl 6-(2-morpholinoethoxy)benzofuran-2-carboxylate収率 73.4%

試薬・触媒・溶媒 1

HCID 18184436N,N-dimethylformamide acetone溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 267 (650 mg, 3.39 mmol) in a 1:1 mixture of DMF-acetone (20 mL) was added 4-(2-chloroethyl)morpholine (630 mg, 3.39 mmol) and potassium carbonate (937 mg, 6.78 mmol). The reaction mixture was stirred at 60° C. for 72 hours. The solvents were removed under reduced pressure and water (50 mL) was added to the residue. 2M Sodium carbonate solution (20 mL) was added and the resultant solution was extracted with ethyl acetate (2×40 mL). The organic phase was separated, dried with sodium sulfate and the solvents removed under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 1:1 ethyl acetate-hexanes, then ethyl acetate, then 9:1 ethyl acetate-methanol. This afforded 268 as a clear oil (760 mg, 73% yield). 1H NMR: (DMSO) δ 7.67-7.63 (m, 2H), 7.32 (s, 1H), 6.98 (d, J=8.5 Hz, 1H), 4.14-4.16 (m, 2H), 3.85 (s, 3H), 3.57-3.55 (m, 4H), 2.88-2.86 (m, 2H), 2.72-2.70 (m, 4H).

後処理

  1. customThe solvents were removed under reduced pressure and water (50 mL)
  2. additionwas added to the residue
  3. addition2M Sodium carbonate solution (20 mL) was added
  4. extractionthe resultant solution was extracted with ethyl acetate (2×40 mL)
  5. customThe organic phase was separated
  6. dry with materialdried with sodium sulfate
  7. customthe solvents removed under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 1:1 ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-954b34f0d0124745931cb1bf0a2476fd
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

関連ノート

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