Water → HCID 19922441, compound

HRID 1681764Notes

Reaction equation

HRID 1681764 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]>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

6

Reactant 3

HCID 962WaterHCID 15296097HCID 15296097, compoundHCID 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, dissolved 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 extracted three times with chloroform: isopropanol (4:1). The combined extracts were washed with brine, dried over magnesium sulfate, 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. extractionextracted three times with chloroform: isopropanol (4:1)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-b1238a9c69f44aeea39ce5c8f0b70349
Source dataset
uspto-grants-1992_12
Patent number
US05173489

Reaction notes

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