Diethyl Ether → HCID 69551345, compound

HRID 984534Notes

Reaction equation

HRID 984534 reaction equation
[C:1]([O:4][CH:5]([CH2:9][CH:10]=[C:11]([CH3:19])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][OH:17])[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OCC)C>C(Cl)Cl>[C:1]([O:4][CH:5]([CH2:9][CH:10]=[C:11]([CH3:19])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][O:17][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1)[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 72615804HCID 72615804, compound

Product 1

HCID 69551345HCID 69551345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

324 mg (1.20 mmol) of a raw product of 3-acetoxy-11-hydroxy-6,10-dimethyl-5-undecen-2-one and 219 μl (202 mg, 2.40 mmol) dihydropyrane was dissolved in 8.5 ml DCM. After addition of 30 mg (0.12 mmol) pyridinium paratoluene sulfonate, the reaction mixture was stirred for 18 hrs at ambient temperature. Then, 25 ml diethylether was added, the resulting organic phase was washed once with 25 ml semiconcentrated NaCl solution, and dried over Na2SO4. After filtration and removal of the solvent in vacuo, the remaining product was purified by flash chromatography (parameters of the chromatography column: 2.0×20.0 cm, ethylacetate/petroleum ether=1:4) on silica gel.

Workup

  1. washthe resulting organic phase was washed once with 25 ml semiconcentrated NaCl solution
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and removal of the solvent in vacuo
  4. customthe remaining product was purified by flash chromatography (parameters of the chromatography column

Sources & evidence

ORD record
ord-0812572329d8412f9c1ac1bcd71bce60
Source dataset
uspto-grants-2005_03
Patent number
US06867333B2

Reaction notes

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