Diethyl Ether → HCID 12547232, compound

HRID 1199858Notes

Reaction equation

Br[CH2:2][CH:3]=[C:4]([F:10])[C:5]([O:8][CH3:9])(F)F.[CH2:11]([Mg]Br)[CH3:12].C([O:17]CC)C>>[F:10]/[C:4](=[CH:3]\[CH2:2][CH2:11][CH3:12])/[C:5]([O:8][CH3:9])=[O:17]

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 54329401HCID 54329401, compound

HCID 178418443HCID 178418443, compound

Product 1

HCID 12547232HCID 12547232, compoundYield 48%

Procedure

1.0 g (4.5 mmol) of 4-bromo-1-methoxy-1,1,2-trifluoro-2-butene was treated with ethylmagnesium bromide (3M, 1.6 mL, 4.8 mmol) in diethyl ether according to the same procedure as Example 4 to give 0.29 g (48%) of methyl (Z)-2-fluoro-2-hexenoate. 1H-NMR (300 MHz, CDCl3): δ 0.92(3H, t), 1.46(2H, q), 2.20(2H, dq, J=2, 8 Hz), 3.80(3H, a), 6.11(1H, dt, J=8, 33Hz).

Sources & evidence

ORD record: ord-aa517993f3bb44bb8cd5537f295276f2
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04902835

Reaction notes

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