Triphenylphosphine → HCID 59366521, compound

HRID 908654Notes

Reaction equation

HRID 908654 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:34])([F:33])[C:22]1[CH:23]=[C:24]([C:28]2[N:29]=[N:30][NH:31][N:32]=2)[CH:25]=[CH:26][CH:27]=1.[Cl:35][C:36]([Cl:52])=[CH:37][CH2:38][O:39][C:40]1[CH:49]=[C:48]([Cl:50])[C:43]([O:44][CH2:45][CH2:46]O)=[C:42]([Cl:51])[CH:41]=1>>[Cl:52][C:36]([Cl:35])=[CH:37][CH2:38][O:39][C:40]1[CH:49]=[C:48]([Cl:50])[C:43]([O:44][CH2:45][CH2:46][N:30]2[N:31]=[N:32][C:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:20])([F:33])[F:34])[CH:23]=3)=[N:29]2)=[C:42]([Cl:51])[CH:41]=1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 7069335-[3-(Trifluoromethyl)phenyl]-2H-tetrazoleHCID 22006767HCID 22006767, compound

Product 1

HCID 59366521HCID 59366521, compoundYield 112.7%

Procedure

Diisopropyl azodicarboxalate (0.056 gram, 0.00028 mole) was added to a stirred, cold (0° C.) mixture of 0.072 gram (0.00028 mole) of triphenylphosphine, 0.045 gram (0.00021 mole) of 5-(3-trifluoromethylphenyl)-2H-1,2,3,4-tetrazole and 0.075 gram (0.00023 mole) of 2-(4-(3,3-dichloroprop-2-enyloxy)-2,6-dichlorophenoxy)ethan-1-ol. The cold reaction mixture stirred for one hour at which time the mixture was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel, eluting with hexanes:ethyl (80:20). The appropriate fractions were combined and concentrated under reduced pressure to yield 0.125 gram of an oil. This oil was combined with similarly obtained oils from three reactions preformed in a similar manner. The combined oil was further purified by column chromatography on silica gel, eluting with mixtures of hexanes, methylene chloride and ethyl acetate to yield 0.267 gram of the subject compound as an oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe cold reaction mixture
  2. concentrationwas concentrated under reduced pressure to a residue
  3. washeluting with hexanes:ethyl (80:20)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c220de6c9c4d4d3c92a98a3bdce12c11
Source dataset
uspto-grants-2011_09
Patent number
US08017635B2

Reaction notes

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