2-Ethyl-2-methyl-1,3-dioxolane → (R)-6-(2-(2-(4-Bromophenyl)-2-o-tolylethyl)-1,3-dioxolan-2-yl)-2-methylpyridazin-3(2H)-one

HRID 1527979ノート

反応式

HRID 1527979 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[N:17]=2)=[O:11])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:39]([C:41]1(C)OCC[O:42]1)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]2([C:12]3[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[N:17]=3)[O:42][CH2:41][CH2:39][O:11]2)=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 610672-Ethyl-2-methyl-1,3-dioxolaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86684807HCID 86684807、化合物

生成物 1

HCID 86684810(R)-6-(2-(2-(4-Bromophenyl)-2-o-tolylethyl)-1,3-dioxolan-2-yl)-2-methylpyridazin-3(2H)-one収率 16.2%

実験手順

A solution of (R)-6-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-2-methylpyridazin-3(2H)-one (example 8, step 3; 235 mg, 571 μmol), and p-toluenesulfonic acid monohydrate (10.9 mg, 57.1 μmol) in 2-ethyl-2-methyl-1,3-dioxolane (2.33 g, 20.0 mmol) was heated for 45 min at 110° C., then partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; gradient heptane-ethyl acetate) produced the title compound (42 mg, 16%). White semisolid, MS: 455.1 [M+H]+.

後処理

  1. custompartitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-f25f85b7f8734bd285844912a2c23187
出典データセット
uspto-grants-2015_07
特許番号
US09090565B2

反応ノート

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