Ozone → HCID 22872598, compound

HRID 1779997Notes

Reaction equation

HRID 1779997 reaction equation
[O:1]=[O+][O-].[CH3:4][C@H:5]([C@@H:18]([CH3:25])[CH2:19][CH2:20][CH:21]=C(C)C)[CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]>O=O.C(Cl)Cl>[CH3:25][C@H:18]([C@@H:5]([CH3:4])[CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:19][CH2:20][CH:21]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 22872576HCID 22872576, compound

Product 1

HCID 22872598HCID 22872598, compound

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stream of 4% ozone in oxygen was bubbled through a solution of 1.79 g (~6 mmol) of 2(R),3(S),7-trimethyl-1-benzyloxycarbonylamino-6-octene in 25 mL of methylene chloride at -78° C. until blue color persisted. Nitrogen gas was bubbled through the reaction mixture at the same temperature for 15 min. 3 mL of dimethyl sulfide was added and the mixture was stirred 15 mins and then warmed to 0° C. The solvents and other volatile materials were removed under house vacuum. Traces of solvent were then removed in vacuo to give 1.3 g of the desired aldehyde as a thick oil.

Workup

  1. customNitrogen gas was bubbled through the reaction mixture at the same temperature for 15 min
  2. addition3 mL of dimethyl sulfide was added
  3. customThe solvents and other volatile materials were removed under house vacuum
  4. customTraces of solvent were then removed in vacuo

Sources & evidence

ORD record
ord-e9c1c55822374f5fae7e1afdf68be22b
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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