Water → HCID 18374023, compound

HRID 2301698Notes

Reaction equation

HRID 2301698 reaction equation
CC(C)([O-])C.[K+].[CH:7]12[CH2:13][CH:10]([CH:11]=[CH:12]1)[CH2:9][CH:8]2[CH:14]=[O:15].Cl[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].O>O1CCCC1.CCCCCC>[O:15]1[CH:14]([CH:8]2[CH2:9][CH:10]3[CH2:13][CH:7]2[CH:12]=[CH:11]3)[CH:17]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 66052tert-Butyl chloroacetateHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 18374023HCID 18374023, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

In a nitrogen atmosphere, a solution of 112 g of potassium tert-butoxide in 400 g of dry tetrahydrofuran was added dropwise over 2 hours to a mixture of 122 g of 5-norbornene-2-carbaldehyde, 151 g of tert-butyl chloroacetate, and 500 g of dry tetrahydrofuran at 0-5° C. After one hour of stirring, 400 g of water was added to stop the reaction. The organic layer obtained by hexane extraction was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by vacuum distillation yielded 224 g (yield 95%) of tert-butyl 2,3-epoxy-3-(5-norbornen-2-yl)propionate as a fraction having a boiling point of 92-94° C./53 Pa.

Workup

  1. customthe reaction
  2. washwas washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. distillationby vacuum distillation

Sources & evidence

ORD record
ord-49833f1306d44210b568a44e3d9a08ce
Source dataset
uspto-grants-2002_12
Patent number
US06500971B2

Reaction notes

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