Pyridine → Triphenylcarbinol

HRID 2397481Notes

Reaction equation

HRID 2397481 reaction equation
C(=C(O)[C@@H](O)[C@@H](O)[C@@H](O)C=[O:9])(C)C.N1C=CC=CC=1.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:21]1([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[OH:9])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 22797331HCID 22797331, compound

Product 1

HCID 6457Triphenylcarbinol

Procedure

To a solution of 3.0 g (15.8 mmoles) of isopropylidene-ribose in 50 ml of absolute pyridine 4.4 g (15.8 mmoles) of trityl chloride are added and the mixture is stirred in a closed flask for 3 days at room temperature. The yellow-brown solution produced is poured into approximately 1 l of ice water. The brown sirup which separates is decanted off and is thoroughly mixed several times with water. Following this this sirup is dissolved in 50 ml of CHCl3 and washed twice with KHSO4 -solution and 3 times with water. After drying over sodium sulfate the solvent is abstracted. A light brown sirup containing crystals remains. By crystallisation from methanol it is possible to obtain 1 g of triphenylcarbinol.

Workup

  1. customThe yellow-brown solution produced
  2. customThe brown sirup which separates is decanted off
  3. dissolutionis dissolved in 50 ml of CHCl3
  4. washwashed twice with KHSO4 -solution and 3 times with water
  5. dry with materialAfter drying over sodium sulfate the solvent
  6. additionA light brown sirup containing crystals
  7. customBy crystallisation from methanol it

Sources & evidence

ORD record
ord-5b9f8cbae03f44899afae8424ca83b1d
Source dataset
uspto-grants-1977_05
Patent number
US04021542

Reaction notes

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