3,4-dihydro-2H-pyran → 6-[2-(2-Ethyloxiran-2-yl)ethyl]-3,4-dihydro-2H-pyran

HRID 647750Notes

Reaction equation

HRID 647750 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.[O:12]1[C:14]([CH2:18][CH3:19])([CH2:15][CH2:16]I)[CH2:13]1>CCCCCC.O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH2:15]([C:14]1([O:12][CH2:13]1)[CH2:18][CH2:19][C:2]1[O:1][CH2:6][CH2:5][CH2:4][CH:3]=1)[CH3:16]

Participants

7

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 132371782-Ethyl-2-(2-iodoethyl)oxiraneHCID 178418306HCID 178418306, compound

Product 1

HCID 132371796-[2-(2-Ethyloxiran-2-yl)ethyl]-3,4-dihydro-2H-pyranYield 86.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a stirred solution of 3.2 g of dihydropyran and 1.4 g of dry tetrahydrofuran at 0° C. was added dropwise 50 ml 2 M tert-butyl lithium. The reaction was allowed to warm to room temperature, then cooled to -10° to -20° C., and 10 g of 1,2-epoxy-2-(ethyl)-4-iodobutane and 0.7 g of hexamethylphosphoramide was added dropwise over 10 minutes. After stirring for 2 hours at -15° to -20° C., 6-8 ml of dry tetrahydrofuran was added. The reaction mixture was allowed to warm to room temperature, stirred for a total of 2 hours, 40-50 ml of hexane was added, and the mixture was washed with water and then with a saturated sodium chloride and sodium bisulfite mixture, dried and vacuum stripped to give 6 g of the desired material as an oil.

Workup

  1. temperaturecooled to -10° to -20° C.
  2. temperatureto warm to room temperature
  3. additionwas added
  4. washthe mixture was washed with water
  5. dry with materialwith a saturated sodium chloride and sodium bisulfite mixture, dried

Sources & evidence

ORD record
ord-2e1d10db8376405e85587d49a5f39ad0
Source dataset
uspto-grants-1983_10
Patent number
US04410354

Reaction notes

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