2-Chloroethyl chloroformate → 6-[2-(2-Hydroxyethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950639ノート

反応式

HRID 1950639 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1.ClC([O:24][CH2:25][CH2:26]Cl)=O>N1C=CC=CC=1>[OH:24][CH2:25][CH2:26][NH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=2[CH2:11]1

参加物

4

反応物 2

HCID 123052-Chloroethyl chloroformateHCID 230873286-(2-Amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

生成物 1

HCID 579337496-[2-(2-Hydroxyethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
180 °C

実験手順

To a solution of 6-(2-amino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol (1.6 g) in pyridine (6 ml) was added dropwise 2-chloroethyl chloroformate (1.4 ml) on an ice bath, and the solution was stirred for 6.5 hours. The solution was diluted with ice water, and then extracted with ethyl acetate. The solution was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. To the residue were added potassium hydroxide (3.0 g) and ethylene glycol (15 ml), and the solution was heated for 3 hours at 180° C. The solution was diluted with ice water, and then extracted with ethyl acetate. The solution was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (800 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe solution was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. additionTo the residue were added potassium hydroxide (3.0 g) and ethylene glycol (15 ml)
  6. additionThe solution was diluted with ice water
  7. extractionextracted with ethyl acetate
  8. washThe solution was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

出典と根拠

ORDレコード
ord-d67491d87c27454aa29a2ae9f083fd8a
出典データセット
uspto-grants-2013_03
特許番号
US08399520B2

反応ノート

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