3,4-dihydro-2H-pyran → 1-Acetoxy-8-(2-tetrahydropyranyl)oxy-3,7-dimethyl-2,6-octadiene

HRID 1707770Notes

Reaction equation

HRID 1707770 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:14])[CH2:12][OH:13])(=[O:3])[CH3:2].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C(=O)(O)[O-].[Na+]>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:15])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:14])[CH2:12][O:13][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][O:16]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 539043298-Acetoxy-2,6-dimethyl-2,6-octadien-1-ol

Product 1

HCID 536575631-Acetoxy-8-(2-tetrahydropyranyl)oxy-3,7-dimethyl-2,6-octadieneYield 96%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-acetoxy-2,6-dimethyl-2,6-octadien-1-ol (1.81 g, 8.52 mmol) and dihydropyran (1.17 ml, 12.8 mmol) in dichloromethane (6 ml) was stirred, and p-toluenesulfonic acid (40 mg) was added thereto, and the mixture was stirred at room temperature for 30 minutes. After addition of saturated aqueous sodium bicarbonate (30 ml), the product was extracted with hexane/ether (5:1.2) (30 ml). The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a residue, which was purified with silica gel column chromatography to give 1-acetoxy-8-(2-tetrahydropyranyl)oxy-3,7-dimethyl-2,6-octadiene (2.42 g, 96%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was extracted with hexane/ether (5:1.2) (30 ml)
  3. dry with materialThe extract was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto remove the solvent
  6. customto give a residue, which
  7. customwas purified with silica gel column chromatography

Sources & evidence

ORD record
ord-13a2eb7552a74f45bbd67ff9a1fb0e97
Source dataset
uspto-grants-1994_10
Patent number
US05354874

Reaction notes

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