Methanol → HCID 19352551, compound

HRID 725682Notes

Reaction equation

HRID 725682 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-acfac7eb83044cf4947eceecc8103bf5
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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