Sodium Hydroxide → 2-(4-Methylsulfonylphenyl)-3-phenylazulene-1-carboxylic acid

HRID 1456824ノート

反応式

HRID 1456824 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:27]([O:29]C)=[O:28])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:27]([OH:29])=[O:28])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 22107203Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate

生成物 1

HCID 221072002-(4-Methylsulfonylphenyl)-3-phenylazulene-1-carboxylic acid収率 79.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 2 -(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate (0.26 g) in MeOH (10.0 ml) was added 10% aqueous NaOH (2.0 ml), and the reaction mixture was heated under reflux for 6 hr. After removal of solvent, the aqueous layer was washed with Et2O. The solution was adjusted to pH 2.0 with 10% aqueous HCl, and extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (EtOAc/MeOH, 30: 1) to give the title compound (0.20 g) as violet crystals; mp 168°-169° C.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 6 hr
  3. customAfter removal of solvent
  4. washthe aqueous layer was washed with Et2O
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by SiO2 column chromatography (EtOAc/MeOH, 30: 1)

出典と根拠

ORDレコード
ord-233133649e0b4c0896354c5153be05f6
出典データセット
uspto-grants-1998_12
特許番号
US05843999

反応ノート

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