p-Toluenesulfonic acid → 4-methyl-4(RS)-tetrahydropyran-2-yloxy-1,5-octadiyne

HRID 26666Notes

Reaction equation

HRID 26666 reaction equation
[CH3:1][C:2]([OH:10])([C:6]#[C:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][C:2]([O:10][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)([C:6]#[C:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 213220394-methyl-1,5-octadiyn-4(RS)-ol

Product 1

HCID 213220474-methyl-4(RS)-tetrahydropyran-2-yloxy-1,5-octadiyne

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Methyl-1,5-octadiyn-4(RS)-ol is reacted with dihydropyran in the presence of p-toluenesulfonic acid in dry benzene to provide 4-methyl-4(RS)-tetrahydropyran-2-yloxy-1,5-octadiyne which in turn is reacted with triethyl tin hydride to provide 4-methyl-4(RS)-tetrahydropyran-2-yloxy-oct-5-yn-trans-1-enyl triethyl tin, having the following structural formula: ##STR12##

Sources & evidence

ORD record
ord-f7c5e08e299e4030a0457aa063a10d76
Source dataset
uspto-grants-1979_04
Patent number
US04151187

Reaction notes

Loading…