Nitromethane → 4-(benzylthio)-4-(nitromethyl)tetrahydro-2H-pyran

HRID 1033831Notes

Reaction equation

HRID 1033831 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N+:16]([CH3:19])([O-:18])=[O:17].N1CCCCC1>C1C=CC=CC=1.O>[CH2:8]([S:15][C:4]1([CH2:19][N+:16]([O-:18])=[O:17])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 8082PiperidineHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 190249354-(benzylthio)-4-(nitromethyl)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

2,3,5,6-Tetrahydropyran-4-one (5 g), benzyl mercaptan (6.2 g), nitromethane (2.7 cm3), and piperidine (1 cm3) were dissolved in benzene (50 cm3), and the mixture heated under reflux with azeotropic removal of water. After 8 days the reaction mixture was allowed to cool and washed first with dilute hydrochloric acid, then with water. The remaining solution was dried and the solvent then removed under reduced pressure to give the nitro system (8g, 60%). This material was sufficiently pure to be used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureto cool
  3. washwashed first with dilute hydrochloric acid
  4. customThe remaining solution was dried
  5. customthe solvent then removed under reduced pressure

Sources & evidence

ORD record
ord-40553c2dc5e046e0a449cc8b2dc7795b
Source dataset
uspto-grants-1994_05
Patent number
US05312904

Reaction notes

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