HCID 22117542, compound → HCID 22117483, compound

HRID 1275790Notes

Reaction equation

HRID 1275790 reaction equation
[C:1]1([C:7]2([O:20][C:21]3([CH:24]([OH:27])CO)[CH2:23][CH2:22]3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1.O.CCOC(C)=O>[C:1]1([C:7]2([O:20][C:21]3([CH:24]=[O:27])[CH2:22][CH2:23]3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]3[C:19]2=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 22117542HCID 22117542, compound

Product 1

HCID 22117483HCID 22117483, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-[1-(9-Phenyl-9-fluorenoxy)cyclopropyl]-1,2-dihydroxyethane in THF:H2O is treated with NalO4 (1.1 eq). The resulting suspension is stirred at room temperature for 4h and then diluted with H2O and EtOAc. The EtOAc extract is washed consecutively with 10% aq sodium thiosulfate solution and then brine. The EtOAc layer is dried (Na2SO4) and concentrated in vacuo. The crude product is purified by filtration through a short pad of silica gel.

Workup

  1. extractionThe EtOAc extract
  2. washis washed consecutively with 10% aq sodium thiosulfate solution
  3. dry with materialThe EtOAc layer is dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. filtrationThe crude product is purified by filtration through a short pad of silica gel

Sources & evidence

ORD record
ord-390be2b0e30f441a94ac2930dd2e308c
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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