Ozone → HCID 85753990, compound

HRID 992838Notes

Reaction equation

HRID 992838 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([C:6]1([CH2:15][CH:16]=C)[C:13](=[O:14])[N-:12][C:10](=[O:11])[NH:9][C:7]1=[O:8])[CH3:5].[Na+].[O:19]=[O+][O-]>CO>[CH3:5][CH:4]([C:6]1([CH2:15][CH:16]=[O:19])[C:7](=[O:8])[NH:9][C:10](=[O:11])[NH:12][C:13]1=[O:14])[CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 24823OzoneHCID 14148199309-43-3

Product 1

HCID 85753990HCID 85753990, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium secobarbital (5.30 g, 22.2 mmol) in methanol was passed a stream of ozone until the solution turned a blue color. After excess ozone was removed by passing nitrogen through the reaction dimethyl sulfide (14 mL) was added. The reaction was stirred at room temperature overnight before solvents were removed on a rotovap. The aldehyde was then purified on silica prep plates using ethyl acetate:hexanes (1:1).

Workup

  1. customAfter excess ozone was removed
  2. customthrough the reaction dimethyl sulfide (14 mL)
  3. additionwas added
  4. customwere removed on a rotovap
  5. customThe aldehyde was then purified on silica prep plates

Sources & evidence

ORD record
ord-297627d4a007406daa837cbd3758e511
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Reaction notes

Loading…