Dichloromethane → methyl 3-(1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate

HRID 218130

反応式

HRID 218130 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C(Cl)Cl.[CH3:21][O:22][C:23]([O:27][Si](C)(C)C)=[C:24]([CH3:26])[CH3:25]>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:24]([CH3:26])([CH3:25])[C:23]([O:22][CH3:21])=[O:27])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 59252753HCID 59252753、化合物

生成物 1

HCID 59251051methyl 3-(1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate収率 66.7%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

(1H-Indazol-5-yl)(phenyl)methanol (12.1 g, 54 mmol) was dissolved in 200 mL of dry THF and 200 mL of DCM and cooled to 0 C. Added 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (43.6, 250 mmol) followed by dropwise addition of TiCl4 (60 mL of 1.0 M DCM solution, 60 mmol). After 12 h, the reaction was quenched with MeOH, poured into brine and extracted 2×DCM. The organic layers were dried over MgSO4, filtered, concentrated, and then chromatographed using 1:2 EtOAc/hexane to give 11.1 g (66% yield) of methyl 3-(1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate which was separated by chiral chromatography. MS found: (M+H)+=309.

後処理

  1. customthe reaction was quenched with MeOH
  2. additionpoured into brine
  3. extractionextracted 2×DCM
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

出典と根拠

ORDレコード
ord-a53d660dca6c4d39bb60e694efeeb4f9
出典データセット
uspto-grants-2012_06
特許番号
US08198311B2

関連ノート

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