Methanol → HCID 57267993, compound

HRID 622109Notes

Reaction equation

HRID 622109 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.N1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18][OH:19]>>[CH2:18]([OH:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH2:17][CH2:6][CH2:1][CH2:2][CH2:3][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:1][CH3:11]

Participants

3

Reactant 2

HCID 887MethanolHCID 161440Pyridine 4-methylbenzene-1-sulfonate

Product 1

HCID 57267993HCID 57267993, compound

Procedure

The mixture of compounds from Example 16(a) (0.24 mole) was dissolved in 3 liters of methanol and pyridine p-toluenesulfonic acid (0.012 mole) was added to the mixture, with stirring under argon at room temperature. The progress of the reaction was monitored by thin layer chromatography. When the reaction was complete the solvent was evaporated and the residue flash chromatographed on silica gel eluted with 90:10 hexane:ethyl acetate to give a 3:1 mixture of the resulting trans:cis isomers. Separation was accomplished by careful chromatography on silica gel.

Workup

  1. customwas evaporated
  2. customthe residue flash chromatographed on silica gel
  3. washeluted with 90:10 hexane
  4. customethyl acetate to give
  5. additiona 3:1 mixture of the resulting trans
  6. customSeparation

Sources & evidence

ORD record
ord-6ad162af024c4f93b7a1dcdd6b1878c8
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Reaction notes

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