Hydrochloric Acid → Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

HRID 900761

反応式

HRID 900761 の反応式
[S:1]1[CH2:6][CH2:5][CH:4]([C:7]#N)[CH2:3][CH2:2]1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC[O:19]CC.Cl>C1COCC1.[Cu]I>[C:9]1([C:7]([CH:4]2[CH2:5][CH2:6][S:1][CH2:2][CH2:3]2)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21598641Thiane-4-carbonitrileHCID 178418255HCID 178418255、化合物

生成物 1

HCID 69290818Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Tetrahydro-2H-thiopyran-4-carbonitrile (2.6 g, 20.5 mmol) and CuI (195 mg, 1 mmol) were diluted in dry THF (200 ml). A 1M solution of phenyl magnesium bromide in THF (41 ml, 41 mmol) was added and the mixture was heated at reflux for 16 hours. After cooling at room temperature, ether was added and the imine was hydrolyzed with a 1 N HCl solution for 10 minutes. The organic phase was separated and treated with a 0.1 N HCl solution for 10 minutes. The organic phase was separated and washed with brine, dried over MgSO4 and evaporated in vacuum. After chromatography on silica gel (CH2Cl2/hexane 30/70), the phenyl(tetrahydro-2H-thiopyran-4-yl)methanone 17 was obtained as a white solid (3 g, 70%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe organic phase was separated
  4. additiontreated with a 0.1 N HCl solution for 10 minutes
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuum

出典と根拠

ORDレコード
ord-dfd66986ba0d4db5a9580e8fab9bfee8
出典データセット
uspto-grants-2008_04
特許番号
US07361668B2

関連ノート

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