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

HRID 900761

Reaction equation

HRID 900761 reaction equation
[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21598641Thiane-4-carbonitrileHCID 178418255HCID 178418255, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-dfd66986ba0d4db5a9580e8fab9bfee8
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Linked notes

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