Pyridine → HCID 53999410, compound

HRID 426781Notes

Reaction equation

HRID 426781 reaction equation
[OH:1][CH:2]1[C:6](=[O:7])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH2:3]1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.N1C=CC=CC=1>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:1][CH:2]1[C:6](=[O:7])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH2:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 80803,4-dihydro-2H-pyran2×HCID 85913006HCID 85913006, compound

Product 1

HCID 53999410HCID 53999410, compound

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of p-toluenesulphonic acid (20 mg) in dry dichloromethane (5 ml) was added, dropwise, to a stirred mixture of methyl (±)-7-[4-hydroxy-5-oxocyclopent-1-enyl]-hepatanoate (1.2 g; prepared as described in Example 3) and 2,3-dihydropyran in dry dichloromethane (20 ml), with cooling to maintain the temperature below 30° C. After one hour, a further quantity of 2,3-dihydropyran (0.3 g) was added dropwise, and the mixture was stirred for one hour further. Pyridine (100 mg) was added, and the mixture was washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, and evaporated in vacuo, finally at 0.1 mm Hg and 50° C. for 4 hours, to give methyl (±)-7-[4-(2-tetrahydropyranyloxy)-5-oxocyclopent-1-enyl]heptanoate (1.9 g), in the form of a brown oil, pure enough for use in the next stage without further purification.

Workup

  1. temperaturewith cooling
  2. temperatureto maintain the temperature below 30° C
  3. washthe mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo, finally at 0.1 mm Hg and 50° C. for 4 hours

Sources & evidence

ORD record
ord-a39bc3c3b25948cb9b9a156aa97c1675
Source dataset
uspto-grants-1979_10
Patent number
US04171375

Reaction notes

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