Water → HCID 11641897, compound

HRID 1158175Notes

Reaction equation

HRID 1158175 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=3)[CH:19]=[CH:20][C:21]=2[CH:22]=[CH2:23])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].CN1C[CH2:40][O:39]CC1.[OH2:42]>ClCCl.[Os](=O)(=O)(=O)=O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=3)[CH:19]=[CH:20][C:21]=2[CH2:22][CH:23]([OH:42])[CH2:40][OH:39])[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 962Water2×HCID 79724-MethylmorpholineHCID 66671882HCID 66671882, compound

Product 1

HCID 11641897HCID 11641897, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

150 mg of ethyl 3″-tert-butyl-4″-diethylamino-4′-vinyl[1,1′;3′,1″]terphenyl-4-carboxylate obtained in Example 32b are dissolved in 10 mL of dichloromethane under a nitrogen atmosphere. 45 mg of N-methylmorpholine are added to the reaction medium, and 0.5 mL of a commercial 2.5% solution of osmium tetroxide in water is then added dropwise and the reaction medium is stirred at room temperature for 3 hours. The reaction is then stopped by adding 10 mL of water and extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate and filtered through a sinter funnel. The solvent is evaporated off and the residue obtained is purified by chromatography on silica (eluent: 7/3 heptane/ethyl acetate). 20 mg of ethyl 3″-tert-butyl-4″-diethylamino-4′-(2,3-dihydroxypropyl)-[1,1′;3′,1″]terphenyl-4-carboxylate are obtained in the form of a white solid.

Workup

  1. additionis then added dropwise
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a sinter funnel
  6. customThe solvent is evaporated off
  7. customthe residue obtained
  8. customis purified by chromatography on silica (eluent: 7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-635deee71a154e6aaa78d40826fca225
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

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