Methanesulfonic Acid → HCID 66766901、化合物

HRID 2195505ノート

反応式

HRID 2195505 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:7][N:6]=[CH:5]2.CS(O)(=O)=O.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl.C1COCC1>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:7]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][O:21]1)[N:6]=[CH:5]2

参加物

6

反応物 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 66766802Ethyl 5-hydroxy-1H-indazole-6-carboxylate

生成物 1

HCID 66766901HCID 66766901、化合物収率 77.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 5-hydroxy-1H-indazole-6-carboxylate (15.5 g, 75 mmol) in DCM (100 mL) and THF (100 mL) containing methanesulfonic acid (721 mg, 7.5 mmol) is added a solution of 3,4-dihydro-2H-pyran (6.6 g, 79 mmol) in DCM (20 mL) dropwise at RT. The resulting solution is stirred at RT overnight. After the solvent is removed, EtOAc (500 mL), saturated aqueous sodium chloride (500 mL) and NaHCO3 (5 g) are added. The organic layer is separated, dried and concentrated. The residue is purified by silica gel column chromatography to afford the product (16.8 g, 77% yield). MS (m/z): 291.1 (M+H).

後処理

  1. customAfter the solvent is removed
  2. additionEtOAc (500 mL), saturated aqueous sodium chloride (500 mL) and NaHCO3 (5 g) are added
  3. customThe organic layer is separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-59db8290479847ba9958bc6270251dbd
出典データセット
uspto-grants-2012_12
特許番号
USRE043878E1

反応ノート

読み込み中…