Water → HCID 19922441, compound

HRID 1463662Notes

Reaction equation

HRID 1463662 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
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-7c70b6ebed884dc9afdd573e9a0f4f36
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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