4-Toluenesulfonyl chloride → 2H-Pyran, 2-(5-hexenyloxy)tetrahydro-

HRID 465573Notes

Reaction equation

HRID 465573 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1.CCOCC>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 80803,4-dihydro-2H-pyranHCID 699635-Hexen-1-ol

Product 1

HCID 111830362H-Pyran, 2-(5-hexenyloxy)tetrahydro-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.5 g 5-hexen-1-ol in 100 ml tetrahydrofuran is added 14 ml dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 h and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H).

Workup

  1. washThe mixture is then washed with saturated aqueous sodium bicarbonate
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting oil is chromatographed over silica gel

Sources & evidence

ORD record
ord-b7fcf94cfff84577a1faee790ca8735e
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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