Water → HCID 22748558, compound

HRID 1390204Notes

Reaction equation

HRID 1390204 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]([O:8][CH3:9])=[O:7].Br[NH:11][C:12](=[O:14])[CH3:13].O.C[CH2:17][O:18]CC>>[CH3:1][O:2][CH2:3][CH:4]1[O:18][CH:17]2[N:11]([C:12](=[O:14])[CH2:13]2)[CH:5]1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4353N-BromoacetamideHCID 641429(E)-methyl 4-methoxybut-2-enoate

Product 1

HCID 22748558HCID 22748558, compound

Procedure

Methyl 4-methoxy-trans-crotonate (6.5 g, 50 m.mole) and N-bromoacetamide (7.6 g, 55 m.mole) were dissolved together in peroxide-free dioxane (30 ml) and water (12 ml) was added. The solution was kept at room temperature in the dark for 7 days. The resulting clear, colourless solution was diluted with ether (150 ml) and washed three times with water (50 ml portions). The solution was dried (MgSO4) and the solvent removed under reduced pressure to yield a colourless oil (9.47 g) which was chromatographed on silica-gel (elution with ethyl acetate/petroleum ether) to give the erythro bromohydrin (e2) as a colourless oil (3.46 g, 30.5%).

Workup

  1. washwashed three times with water (50 ml portions)
  2. dry with materialThe solution was dried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cd854b187a6245b680522a34a82962cd
Source dataset
uspto-grants-1979_02
Patent number
US04138403

Reaction notes

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