Water → 3-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 131164

反応式

HRID 131164 の反応式
[CH:1]1[C:10]2CCCC[C:5]=2C=C[C:2]=1[OH:11].O.Cl[C:14]1[C:15](=O)[C:16](C#N)=[C:17]([C:22]#[N:23])[C:18](=[O:21])[C:19]=1Cl>O1CCOCC1>[OH:21][C:18]1[C:17]([C:22]#[N:23])=[CH:16][C:15]2[C:2](=[O:11])[CH2:1][CH2:10][CH2:5][C:14]=2[CH:19]=1

参加物

5

反応物 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 143055,6,7,8-Tetrahydro-2-naphthol

生成物 1

HCID 218649643-Hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile収率 40%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

5,6,7,8-tetrahydro-2-naphthalenol prepared in method II-2 (1.5 g, 8.7 mmol) was dissolved in 1,4-dioxane (8 mL) in a 100 mL round bottom flask. To this was added water (2 mL), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (4.1 g, 18.2 mmol, 2.1 eq) in anhydrous 1,4-dioxane (16 mL) dropwise. The reaction mixture turned to black immediately after addition and resulting mixture was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was evaporated in vacuo. The residue was participated between EtOAc and saturated aqueous sodium bicarbonate. The aqueous layer was acidified to about pH 3 and was extracted with EtOAc three times. The organic layers were combined and evaporated in vacuo. Purification using MPLC chromatography (Biotage) gave 0.64 g (40%) of 3-hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile as a light brown solid.

後処理

  1. additionafter addition
  2. customresulting mixture
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. extractionwas extracted with EtOAc three times
  6. customevaporated in vacuo
  7. customPurification

出典と根拠

ORDレコード
ord-815755940eb54b9fb76ce055bcfda58e
出典データセット
uspto-grants-2008_06
特許番号
US07384947B2

関連ノート

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