Hydrochloric Acid → 1-((2-Benzoylphenylthio)methyl)cyclohexanecarboxaldehyde

HRID 2229508

反応式

HRID 2229508 の反応式
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].S([O:20][CH2:21][C:22]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(C)(=O)=O.C(N(CC)CC)C.Cl>COCCOCCOC>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[S:1][CH2:28][C:22]1([CH:21]=[O:20])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 34997132-MercaptobenzophenoneHCID 223252611-(Mesyloxymethyl)cyclohexanecarboxaldehyde

生成物 1

HCID 223252081-((2-Benzoylphenylthio)methyl)cyclohexanecarboxaldehyde収率 75.9%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

A mixture of 69 g (0.303 mole) of 2-mercaptobenzophenone, 82 g (0.303 mole) of mesylate 55, 32 g of triethylamine, and 150 ml of diglyme was stirred and held at reflux for 24 h. The mixture was cooled, poured into dil. HCl and extracted with methylene chloride. The organic layer was washed with 10% NaOH, water, brine, and dried over sodium sulfate and concentrated under vacuum to remove excess diglyme. This was purified by silica gel flush column (5% EtOAc:Hexane) and gave 18.6 g (75.9%) of yellow oil. Proton NMR and mass spectra were consistent with the product.

後処理

  1. temperatureat reflux for 24 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with 10% NaOH, water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto remove excess diglyme
  8. customThis was purified by silica gel
  9. customflush column (5% EtOAc:Hexane)

出典と根拠

ORDレコード
ord-2f71fdaa36f94a28b4301990659889dc
出典データセット
uspto-grants-2002_07
特許番号
US06420417B1

関連ノート

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