Water → HCID 19922441, compound

HRID 1648135Notes

Reaction equation

HRID 1648135 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9]2)=[CH:3][CH:2]=1.S(=O)(O)[O-:31].[Na+].[OH2:35].C(Cl)(Cl)Cl.C(O)(C)C>N1C=CC=CC=1.[Os](=O)(=O)(=O)=O>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][C:8]2([CH2:23][C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([OH:35])[CH:9]2[OH:31])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 15296097HCID 15296097, compoundHCID 21906603Chloroform isopropyl alcoholHCID 23665763Sodium Bisulfite

Product 1

HCID 19922441HCID 19922441, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 1049PyridineSolvent2×

Procedure

To a solution of 1,1-Bis(4-pyridinylmethyl)-3-phenyl-1H-indene (1.0 g, 2.7 mmol) in dry pyridine (10 ml) was added osmium tetroxide (1.0 g, 3.9 mmol, dissoleved in ether). The mixture was stirred at room temperature and monitored by TLC. After completion of the reaction, sodium bisulfite (2.0 g), water (20 ml), and pyridine (5 ml) was added. The mixture was stirred for 1 h, and extractd three times with chloroform: isopropanol (4:1). The combined extracts were washed with brine, dried over magnesium sulfater, and evaporated to give 3,3-bis(4-pyridinylmethyl)-2,3-dihydro-1-phenyl-1H-indene-1,2-diol as a yellow solid, 1.15 g.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 1 h
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over magnesium sulfater
  5. customevaporated

Sources & evidence

ORD record
ord-6f7a1099a4c84b7fb7a3767ffe389987
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

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