Methyl Bromide → ethyl 3-(tetrahydro-2H-pyran-4-yl)-2-propenoate

HRID 1588361Notes

Reaction equation

HRID 1588361 reaction equation
[Mg].BrC.Cl[CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.CN(C)[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1>[O:8]1[CH2:9][CH2:10][CH:5]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6323Methyl BromideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 1372022H-Pyran, 4-chlorotetrahydro-HCID 5462224Magnesium

Product 1

HCID 54040092ethyl 3-(tetrahydro-2H-pyran-4-yl)-2-propenoateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

9.6 g (400 mmol) of magnesium turnings are covered with tetrahydrofuran, about 2 ml of bromomethane are added, and the mixture is warmed to reflux. 38.45 g (300 mmol) of 4-chlorotetrahydropyran, dissolved in 100 ml of tetrahydrofuran, are added dropwise. The mixture is subsequently stirred for a further 30 minutes and cooled to 10° C., 42.9 g (300 mmol) of ethyl 1-(dimethylamino)eth-1-ene-2-carboxylate are added dropwise, and the mixture is stirred for a further 12 hours. Customary work-up gives 31.4 g (60%) of ethyl 1-(4-tetrahydropyranyl)eth-1-ene-2-carboxylate of boiling point 120° to 140° C./10 mmHg.

Workup

  1. additionare added
  2. temperaturethe mixture is warmed to reflux
  3. additionare added dropwise
  4. stirringthe mixture is stirred for a further 12 hours

Sources & evidence

ORD record
ord-0c7a9b567dc44acd818cd55b776051f9
Source dataset
uspto-grants-1993_06
Patent number
US05221753

Reaction notes

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