Triphenylphosphine → 1,1-Dimethylethyl cyclopropyl[(2,3-dichloro-5-formylphenyl)methyl]carbamate

HRID 337566Notes

Reaction equation

HRID 337566 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH:19]=C)[CH:16]=[C:15]([Cl:21])[C:14]=2[Cl:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[O:23]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH:19]=[O:23])[CH:16]=[C:15]([Cl:21])[C:14]=2[Cl:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 668954141,1-Dimethylethyl cyclopropyl[(2,3-dichloro-5-ethenylphenyl)methyl]carbamate

Product 1

HCID 866516631,1-Dimethylethyl cyclopropyl[(2,3-dichloro-5-formylphenyl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (0.03 M) solution of 1,1-dimethylethyl cyclopropyl[(2,3-dichloro-5-ethenylphenyl)methyl]carbamate (1 eq.) from Step 2, Amine 6 was bubbled at −78° C. freshly generated ozone until a persistent blue color was obtained. To this was then added triphenylphosphine (1.2 eq.) in one rapid portion and the resulting mixture was slowly warmed to RT over 3 h. The volatiles were removed in vacuo and the remaining residue was triturated with 2:1 (v/v) Hex:Et2O. The insolubles were removed via filtration and the filtrate was concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customwas obtained
  2. customThe volatiles were removed in vacuo
  3. customthe remaining residue was triturated with 2:1 (v/v)
  4. customThe insolubles were removed via filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the crude product
  7. customthus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-3613fc659d2e4b0488fbd1a459e6747a
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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