Sodium periodate → HCID 69944598, compound

HRID 1682770Notes

Reaction equation

HRID 1682770 reaction equation
C(O[C@H](C1N(C2C=CC=CC=2)N=CC=1)[C@H](C1C=CC(Cl)=C(Cl)C=1)CC=O)(=O)C.C([O:32][C@H:33]([C:46]1[N:50]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:49]=[CH:48][CH:47]=1)[C@H:34]([C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[C:40]([Cl:45])[CH:39]=1)[CH2:35][CH:36]=[CH2:37])(=O)C.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.C(OCC)C.O.[Os](=O)(=O)(=O)=O>[Cl:45][C:40]1[CH:39]=[C:38]([C@H:34]([CH2:35][CH:36]=[CH2:37])[C@@H:33]([C:46]2[N:50]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[N:49]=[CH:48][CH:47]=2)[OH:32])[CH:43]=[CH:42][C:41]=1[Cl:44]

Participants

8

Reactant 3

HCID 23667635Sodium periodateHCID 67717817HCID 67717817, compoundHCID 86750903HCID 86750903, compound

Product 1

HCID 69944598HCID 69944598, compoundYield 110%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[(1S,2S)-1-Acetoxy-2-(3,4-dichlorophenyl)-4-oxobutyl]-1-phenylpyrazole.A solution of 5-[(1S,2S)-1-acetoxy-2-(3,4-dichlorophenyl)-4-pentenyl]-1-phenylpyrazole (90 mg) in tetrahydrofuran (1 mL), diethyl ether (2 mL) and water (2 mL) was treated with osmium tetraoxide (0.07 mL of a 0.2M solution in water) and sodium periodate (100 mg). The resulting biphasic mixture was stirred vigorously at room temperature for 4 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed (brine), dried, and evaporated to afford the title compound as a pale amber foam (89 mg). This material was used immediately; NMR: 9.57 (s,1), 7.62 (d,1), 7.45-7.21 (m,6), 6.99 (d,1), 6.72 (dd,1), 6.31 (d,1), 6.15 (d,1), 3.63 (m,1), 2.77 (m,2), 2.03 (s,3); MS: m/z=419((M+1), 37Cl), 417((M+1), 35Cl).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed (brine)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-f97a56616c4542118bbdbefe175144db
Source dataset
uspto-grants-1997_06
Patent number
US05635509

Reaction notes

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