p-Toluenesulfonic acid → HCID 21521689, compound

HRID 918272Notes

Reaction equation

HRID 918272 reaction equation
C#C[CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7]C.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=[O:23])=CC=1>>[O:10]1[CH:11]=[CH:12][CH:13]=[C:14]([O:23][C:6]2[CH2:7][O:9][CH:3]=[CH:4][CH:5]=2)[CH2:15]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 131661-Octyn-3-ol

Product 1

HCID 21521689HCID 21521689, compound

Procedure

Typically, 1-octyn-3-ol is allowed to react with dihydropyran in the presence of a catalytic amount of p-toluenesulfonic acid to form the 3-pyranyl ether. 3-(tetrahydropyran-2-yl)oxy-1-octyne. That material is treated with diisobutyl aluminum hydride, then with iodine, to yield the corresponding iodo-octene, 3-(tetrahydropyran- 2-yl)oxy-1-iodo-1-octene. Magnesium metal, activated with mercuric chloride, is added to the iodo-octene and that addition is followed by the addition of cuprous iodide to yield 3-(tetrahydropyran-2-yl)oxy-trans-1-octenyl copper.

Sources & evidence

ORD record
ord-49f8c72e7caa415b8c16f34ecb82213c
Source dataset
uspto-grants-1976_07
Patent number
US03970683

Reaction notes

Loading…