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

HRID 131164노트

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HRID 131164 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-815755940eb54b9fb76ce055bcfda58e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384947B2

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