Methanol → HCID 19352551, compound

HRID 378188Notes

Reaction equation

HRID 378188 reaction equation
[CH2:1]([O:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29]C(C3CCCCO3)C)=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH2:38].[C:39]1([CH3:49])C=CC(S(O)(=O)=O)=CC=1.CO.O>C(Cl)(Cl)Cl>[CH2:1]([O:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29][CH:39]([OH:38])[CH3:49])=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 19352714HCID 19352714, compound

Product 1

HCID 19352551HCID 19352551, compoundYield 535.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

At 25° C., 6.7 g (12 mmol) of the 5-undecyloxy-2-[4-{6-(2-tetrahydropyranyl)-1-trans-heptenyl}-phenyl]-pyrimidine obtained in Example 13, 0.4 g (2 mmol) of p-toluenesulfonic acid hydrate, 50 ml of methanol and 5 ml of water were stirred for two hours. Then, water was added and the mixture was extracted with ether. The organic layer was washed with water and dried, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 4.7 g (yield 90%) of (-)-5-undecyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}-pyrimidine, [α]D20 =-1.1 (c=1.3, CHCl3).

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b729329644934413956549cab7e401ce
Source dataset
uspto-grants-2000_02
Patent number
US06030546

Reaction notes

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