p-Toluenesulfonic acid → Methyl 2-methyl-7-nitro-2,3-dihydrobenzofuran-4-carboxylate

HRID 2364731ノート

反応式

HRID 2364731 の反応式
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>ClCCCl>[CH3:3][CH:2]1[CH2:1][C:4]2=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[C:13]2[O:14]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59768300Methyl 2-allyl-3-hydroxy-4-nitro-benzoate

生成物 1

HCID 68107419Methyl 2-methyl-7-nitro-2,3-dihydrobenzofuran-4-carboxylate収率 12.8%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Methyl 2-allyl-3-hydroxy-4-nitro-benzoate 1d (800 mg, 3.30 mmol) was dissolved in 10 mL of 1,2-dichloroethane followed by the addition of 1 mL of p-toluenesulfonic acid. The reaction solution was stirred for 48 hours. The resulting solution was added with 10 mL of saturated sodium bicarbonate solution and extracted with dichloromethane (20 mL×3). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 2-methyl-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 30a (100 mg, yield: 12.5%) as a yellow solid.

後処理

  1. extractionextracted with dichloromethane (20 mL×3)
  2. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-51351d0447ac4bdabd5a60488bdc8bee
出典データセット
uspto-grants-2014_04
特許番号
US08691822B2

反応ノート

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