Pyridine → HCID 22941789, compound

HRID 650336Notes

Reaction equation

HRID 650336 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([OH:23])=[CH:15][C:14]=1[CH2:13][C@H:12]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:3])[CH3:2].[O:33]1[CH:38]=[CH:37][CH2:36][CH2:35][CH2:34]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>O1CCCC1.C(OCC)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][O:33]2)=[CH:15][C:14]=1[CH2:13][C@H:12]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 22941788HCID 22941788, compound

Product 1

HCID 22941789HCID 22941789, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21.3 g of 17β-acetoxy-7α-(5-acetoxypentyl)-estra-1,3,5(10)-trien-3-ol in 213 ml of tetrahydrofuran is allowed to stand with 21.3 ml of 3,4-dihydro-2H-pyran and 1.065 g of p-toluenesulfonic acid for 8 hours at room temperature. The reaction solution is mixed with 3 ml of pyridine, then diluted with diethyl ether, washed with water and dried. The residue that is obtained after the concentration by evaporation is chromatographed on silica gel, and 24.3 g of 17β-acetoxy-7α-(5-acetoxypentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene is obtained as oil. [α]D22=+31.5°(c=0.535% in chloroform)

Workup

  1. washwashed with water
  2. customdried
  3. customThe residue that is obtained
  4. concentrationafter the concentration
  5. customby evaporation
  6. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-1be727cdc0794735952612fcdf96d64f
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

Loading…