Pyridine → HCID 21055313, compound

HRID 2215262Notes

Reaction equation

HRID 2215262 reaction equation
[OH:1][CH2:2][C@H:3]([OH:14])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].N1C=CC=CC=1.[C:21]1([C:27](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[C:21]1([C:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:1][CH2:2][C@H:3]([OH:14])[CH2:4][S:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 21055312HCID 21055312, compound

Product 1

HCID 21055313HCID 21055313, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.3 g (0.09 mol) of 1-(3-hydroxy-2-(S)-hydroxy-propylthio)-2-methoxybenzene (XI-1), 150 ml of acetonitrile, 11 ml (0.136 mol) of pyridine and 27.5 g (0.098 mol) of triphenylmethyl chloride are introduced into a round-bottomed flask under an inert atmosphere. The solution is stirred at ambient temperature for 5 hours. The mixture is concentrated under reduced pressure and the residual pyridine is entrained by azeotropic distillation with toluene. The residue is taken up in water and then extracted with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and evaporated, and the residue is purified by flash chromatography on silica gel (eluent: cyclohexane/dichloromethane=30:70). 34.8 g (0.076 mol) of the title compound (XII-1) are recovered in the form of a yellow oil.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. distillationthe residual pyridine is entrained by azeotropic distillation with toluene
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue is purified by flash chromatography on silica gel (eluent: cyclohexane/dichloromethane=30:70)

Sources & evidence

ORD record
ord-3ea52db4efa442ba952eac0afcdac709
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

Loading…