Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → HCID 59251069、化合物

HRID 218124

反応式

HRID 218124 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27]([O:31][Si](C)(C)C)=[C:28]([CH3:30])[CH3:29]>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:28]([CH3:30])([CH3:29])[C:27]([O:26][CH3:25])=[O:31])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 59251034HCID 59251034、化合物

生成物 1

HCID 59251069HCID 59251069、化合物収率 81%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

(1-(4-Fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (16.0 g, 50 mmol) was dissolved in 400 mL of dry THF and TiCl4 (60 mL of 1.0 M DCM solution, 60 mmol) was added portionwise and then stirred 30 min. The flask was put on a rotary evaporator until the THF began to distill to degas the HCl and then the reaction was treated with 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (17.4 g, 100 mmol). The reaction was quenched with aqueous sodium bicarbonate and extracted 2× EtOAc, the organic layers dried over MgSO4, filtered, concentrated, and then chromatographed using DCM to give 16.2 g (81% yield) of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanoate. MS found: (M+H)+=403.

後処理

  1. customThe flask was put on a rotary evaporator until the THF
  2. distillationto distill
  3. customto degas the HCl
  4. customThe reaction was quenched with aqueous sodium bicarbonate
  5. extractionextracted 2× EtOAc
  6. dry with materialthe organic layers dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed

出典と根拠

ORDレコード
ord-43dc884a223c4fae8ac401014e83c61e
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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