p-Toluenesulfonic acid → HCID 13208202, compound

HRID 2309130Notes

Reaction equation

HRID 2309130 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:17]([OH:18])[CH2:16][C@H:15]2[C@@H:11]1[CH2:12][C:13](=[O:19])[O:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CCOCC.C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@H:10]1[C@H:17]([O:18][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][O:20]2)[CH2:16][C@H:15]2[C@@H:11]1[CH2:12][C:13](=[O:19])[O:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 11459681HCID 11459681, compound

Product 1

HCID 13208202HCID 13208202, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 14.5 g. of (1S,5R,6S,7R)-6-benzyloxymethyl-7-hydroxy-2-oxabicyclo[3,3,0]octan-3-one, 6 ml. of dihydropyran, and 40 mg. of p-toluenesulfonic acid in 300 ml. of absolute methylene chloride as agitated for one hour at 5°. Then the solution is diluted with ether, shaken with 4% sodium bicarbonate solution, washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum. Yield: 21 g. of the tetrahydropyranyl ether as a colorless oil.

Workup

  1. washwashed neutral with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-ae958a91723b42899873c9a9f23ca92e
Source dataset
uspto-grants-1987_09
Patent number
US04692464

Reaction notes

Loading…