HCID 67148403, compound → HCID 86632369, compound

HRID 2428150Notes

Reaction equation

HRID 2428150 reaction equation
O=[O+][O-].[O:4]=O.[C:6]([O:10][C:11](=[O:26])[N:12]([CH2:16][C:17]1[CH:22]=[C:21]([CH:23]=C)[CH:20]=[CH:19][C:18]=1[Cl:25])[CH:13]1[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7]>C(Cl)Cl.CO>[C:6]([O:10][C:11](=[O:26])[N:12]([CH2:16][C:17]1[CH:22]=[C:21]([CH:23]=[O:4])[CH:20]=[CH:19][C:18]=1[Cl:25])[CH:13]1[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 67148403HCID 67148403, compoundHCID 131711318Oxygen ozone

Product 1

HCID 86632369HCID 86632369, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A O3/O2-mixture (generated by a Fischer ozonolyser) was gently bubbled through a sol. of (2-chloro-5-vinyl-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (10.0 g, 32.5 mmol) in CH2Cl2 (356 mL) and MeOH (44 mL) at −78° C. for 60 min. The mixture turned light blue, and pure O2 was bubbled through the mixture until it became colourless. The mixture was purged with a stream of nitrogen for 60 min, and Me2S (44.0 mL) was added. The mixture was stirred at −78° C. for 2 h. The solvents were removed under reduced pressure, and the residue was dried under high vacuum overnight to yield to crude title compound (11.7 g, quantitative yield) that was used further without purification. LC-MS: tR=1.04 min; ES+: 295.34.

Workup

  1. custompure O2 was bubbled through the mixture until it
  2. customThe mixture was purged with a stream of nitrogen for 60 min
  3. additionMe2S (44.0 mL) was added
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was dried under high vacuum overnight

Sources & evidence

ORD record
ord-7924cc9ae53b44549ce34fe66587dd9f
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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