Diethyl Ether → HCID 19764334, compound

HRID 248174Notes

Reaction equation

HRID 248174 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:35])([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:9](=[CH2:18])[CH2:10][CH:11]([CH3:17])[C:12](OCC)=[O:13].CC[O:38]CC>>[F:35][C:8]([F:7])([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:9](=[CH2:18])[CH2:10][CH:11]([CH2:12][OH:13])[CH2:17][OH:38]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 21226445Aluminium lithium hydrideHCID 54316357HCID 54316357, compound

Product 1

HCID 19764334HCID 19764334, compound

Procedure

To a slurry of 250 mg of lithium aluminum hydride in 10 ml of ether, cooled to 0° C. is added dropwise a solution of 1.48 g of ethyl (3,3-difluoro-2-methylene-nonadecyl)propanoate in 10 ml of ether followed by warming to ambient temperature, heating at reflux for 3 hours, then allowing to cool to ambient temperature. The reaction mixture is washed with dilute hydrochloric acid, water and dilute sodium bicarbonate, dried and evaporated to a gum which is purified on silica gel using 40-60% ethyl acetate:hexanes. The fractions containing product are collected, evaporated and the residue crystallized from hexane giving 1.04 g of the desired product.

Workup

  1. temperatureheating
  2. temperatureat reflux for 3 hours
  3. temperatureto cool to ambient temperature
  4. washThe reaction mixture is washed with dilute hydrochloric acid, water and dilute sodium bicarbonate
  5. customdried
  6. customevaporated to a gum which
  7. customis purified on silica gel using 40-60% ethyl acetate
  8. additionThe fractions containing product
  9. customare collected
  10. customevaporated
  11. customthe residue crystallized from hexane giving 1.04 g of the desired product

Sources & evidence

ORD record
ord-961743d36ec64c858d6cc1481649fef0
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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