Triethylamine → Methanesulfonic acid 2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-ethyl ester

HRID 456597ノート

反応式

HRID 456597 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15](=[O:17])[NH:14][C:13]=2[CH:18]=1.C(N(CC)CC)C>O1CCCC1>[O:17]=[C:15]1[NH:14][C:13]2[CH:18]=[C:9]([CH2:8][CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[CH:11][C:12]=2[O:16]1

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chloride2 回HCID 179812295-(2-Hydroxy-ethyl)-3H-benzoxazol-2-one

生成物 1

HCID 86760443Methanesulfonic acid 2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-ethyl ester収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methanesulfonyl chloride (0.23 ml, 2.93 mmol) was added dropwise, at room temperature, to a solution of alcohol (b) (0.5 g, 2.79 mmol) and triethylamine (0.41 ml, 3 mmol) in tetrahydrofuran (20 ml) and the mixture was stirred for 3 hours. More methane sulfonyl chloride (0.1 ml) and triethylamine (0.1 ml) were added and stirring was continued over night. The same amount of reagent was added yet again and stirring continued for 2 hours. The solvent was then concentrated, the residue was suspended in water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated. The solid residue was chromatographed on silica gel eluting with heptane-ethyl acetate (1-1) to give the product (0.2 g, 28%).

後処理

  1. stirringstirring
  2. waitwas continued over night
  3. additionThe same amount of reagent was added yet again
  4. stirringstirring
  5. waitcontinued for 2 hours
  6. concentrationThe solvent was then concentrated
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe solid residue was chromatographed on silica gel eluting with heptane-ethyl acetate (1-1)

出典と根拠

ORDレコード
ord-771d18febf8d47fd9363ab5311ab34fe
出典データセット
uspto-grants-2007_03
特許番号
US07186730B2

反応ノート

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