Allyl bromide → HCID 86690122, compound

HRID 520417Notes

Reaction equation

HRID 520417 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([CH:13]=[CH2:14])[C:5]([OH:12])([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].Br[CH2:17][CH:18]=[CH2:19]>CN(C=O)C.CCOCC>[CH2:19]([O:12][C:5]([CH3:11])([C:4]([F:15])([F:3])[CH:13]=[CH2:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86690123HCID 86690123, compound

Product 1

HCID 86690122HCID 86690122, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

60% NaH (48.5 mg, 1.212 mmol) was added to a cold (−20° C.) solution of ethyl 3,3-difluoro-2-hydroxy-2-methylpent-4-enoate (214 mg, 1.102 mmol) in DMF (2 mL) and the mixture was allowed to warm to rt (˜30 min) and then 3-bromoprop-1-ene (0.113 mL, 1.323 mmol) was added. The mixture was stirred at rt overnight, diluted with ether (20 mL) and washed with water, brine and dried (MgSO4). The crude product was purified by silica gel FCC (2:1 DCM-hexanes) to afford ethyl 2-(allyloxy)-3,3-difluoro-2-methylpent-4-enoate as a clear oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. customThe crude product was purified by silica gel FCC (2:1 DCM-hexanes)

Sources & evidence

ORD record
ord-76438c0014b748c584d2b9f3452194ba
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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