1-Chloroethyl chloroformate → 2-[4-(2,6-Dichloro-phenoxymethyl)-phenyl]-morpholine

HRID 920561ノート

反応式

HRID 920561 の反応式
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[CH:16][CH:15]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl:28][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:29])[C:22]=1[O:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:19][CH:18]=1

参加物

4

反応物 2

HCID 5213051-Chloroethyl chloroformateHCID 670325914-Benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholine

生成物 1

HCID 670324202-[4-(2,6-Dichloro-phenoxymethyl)-phenyl]-morpholine収率 78.3%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 4-benzyl-2-[4-(2,6-dichloro-phenoxymethyl)-phenyl]-morpholine (2.25 g; 3.7 mmol) in 1,2-dichloroethane (10 mL), was added dropwise 1-chloroethyl chloroformate (0.44 mL; 4.0 mmol), at 0° C. After 15 minutes, the cooling was removed and subsequently the mixture was heated under reflux overnight. After cooling to RT the mixture was concentrated in vacuo. To the residue was added toluene and the mixture was concentrated in vacuo. This last step was repeated twice. To the final residue was added MeOH (10 mL), and this mixture was stirred overnight at RT. Once more the mixture was concentrated in vacuo. The residue was partitioned between EtOAc and 2 M Aqueous NaOH. The layers were separated, and the organic layer dried (Na2SO4), filtered, and concentrated in vacuo to afford 2-[4-(2,6-Dichloro-phenoxymethyl)-phenyl]-morpholine (0.98 g), which was used as such in the next step.

後処理

  1. customat 0° C
  2. customthe cooling was removed
  3. temperaturesubsequently the mixture was heated
  4. temperatureunder reflux overnight
  5. concentrationwas concentrated in vacuo
  6. additionTo the residue was added toluene
  7. concentrationthe mixture was concentrated in vacuo
  8. additionTo the final residue was added MeOH (10 mL)
  9. concentrationOnce more the mixture was concentrated in vacuo
  10. customThe residue was partitioned between EtOAc and 2 M Aqueous NaOH
  11. customThe layers were separated
  12. dry with materialthe organic layer dried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-287be600da8b4c57956cec6a7d9182f3
出典データセット
uspto-grants-2016_03
特許番号
US09273017B2

反応ノート

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