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

HRID 496168

反応式

HRID 496168 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.CCOCC(OCC)COCC.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 5483211,2,3-TriethoxypropaneHCID 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 triethyline, and 150 ml of diglyme was stirred and held at relux 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. temperatureThe mixture was cooled
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with 10% NaOH, water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto remove excess diglyme
  7. customThis was purified by silica gel
  8. customflush column (5% EtOAc-Hexane)

出典と根拠

ORDレコード
ord-0d3ac92f940f487a82ba14c43666dd6f
出典データセット
uspto-grants-2005_09
特許番号
US06943189B2

関連ノート

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