Diethyl Ether → HCID 19764370, compound

HRID 1885481Notes

Reaction equation

HRID 1885481 reaction equation
[F:1][C:2]([F:24])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])C(OCC)=O.[CH3:25][Mg]Br.CC[O:30][CH2:31][CH3:32]>>[F:1][C:2]([F:24])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:31]([CH3:32])([OH:30])[CH3:25]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 13962353HCID 13962353, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19764370HCID 19764370, compound

Procedure

To a solution of 6.9 g of ethyl 2,2-difluorooctadecanoate in 100 ml of ether at 0° C. is added 33 ml of methyl magnesium bromide dropwise with stirring. Following complete addition the reaction is allowed to reach room temperature and stirred for 30 minutes. The reaction mixture is washed with saturated ammonium chloride solution. The organic layer is washed with 10% hydrochloric acid, water and 10% sodium bicarbonate. The organic layer is dried and evaporated to an oil which is purified by chromatography on silica gel using 1-10% ethyl acetate:hexanes to give 3.8 g of the desired product as a solid following petroleum ether crystallization.

Workup

  1. additionaddition the reaction
  2. customto reach room temperature
  3. stirringstirred for 30 minutes
  4. washThe reaction mixture is washed with saturated ammonium chloride solution
  5. washThe organic layer is washed with 10% hydrochloric acid, water and 10% sodium bicarbonate
  6. customThe organic layer is dried
  7. customevaporated to an oil which
  8. customis purified by chromatography on silica gel using 1-10% ethyl acetate
  9. customhexanes to give
  10. custom3.8 g of the desired product as a solid following petroleum ether crystallization

Sources & evidence

ORD record
ord-914c2dbfaaeb4f95bbbe44abdab26e95
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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