Ammonium Chloride → 6-Cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one

HRID 1474340ノート

反応式

HRID 1474340 の反応式
[CH:1]1([C:4]2[C:5]([CH2:14][CH2:15]O)=[CH:6][C:7]3[CH2:11][O:10][C:9](=[O:12])[C:8]=3[CH:13]=2)[CH2:3][CH2:2]1.CS(Cl)(=O)=O.[Cl-].[NH4+].C1CCN2C(=NCCC2)CC1>O.ClCCl>[CH:1]1([C:4]2[C:5]([CH:14]=[CH2:15])=[CH:6][C:7]3[CH2:11][O:10][C:9](=[O:12])[C:8]=3[CH:13]=2)[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 666466836-Cyclopropyl-5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one

生成物 1

HCID 666463936-Cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a 100 ml flask containing a stir bar was added compound 6-cyclopropyl-5-(2-hydroxyethyl)-2-benzofuran-1(3H)-one, (0.5 g, 2.29 mmol), TEA (20 mL) followed by addition of dichloromethane (25 mL). The flask was placed in a cool bath of ° C., and slowly treated with methanesulfonyl chloride (6.5 mL, 83 mmol). The resulting mixture was then stirred for 20 min. TLC (hexanes/EtOAc=1/1) indicated completion of the reaction. The mixture was poured into saturated ammonium chloride and extracted with DCM. The combined organics were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine, then dried (Na2SO4) and concentrated in vacuo. The residue (LC/MS: [(M+1)]+=297; tR=1.01 min) was dissolved in dichloromethane (25 mL) and treated with DBU (0.7 mL, 4.72 mmol) and stirred for 2 h. TLC monitoring showed conversion to the olefin. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organics were washed with 1N HCl, saturated sodium bicarbonate solution, and brine, then dried (Na2SO4) and concentrated in vacuo. The material was used in the next step without further purification.

後処理

  1. additionTo a 100 ml flask containing a stir bar
  2. customThe flask was placed in a cool bath of ° C
  3. customcompletion of the reaction
  4. extractionextracted with DCM
  5. washThe combined organics were washed with 1 N HCl, saturated sodium bicarbonate solution, and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue (LC/MS: [(M+1)]+=297; tR=1.01 min) was dissolved in dichloromethane (25 mL)
  9. stirringstirred for 2 h
  10. extractionextracted with dichloromethane
  11. washThe combined organics were washed with 1N HCl, saturated sodium bicarbonate solution, and brine
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated in vacuo
  14. customThe material was used in the next step without further purification

出典と根拠

ORDレコード
ord-efa36289ccfb44f18697c92d7a21135d
出典データセット
uspto-grants-2015_04
特許番号
US09018211B2

反応ノート

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