Water → Diethyl 2-formylamino-4-bromomethyl-hept-3-ene-1,7-dicarboxylate

HRID 654656Notes

Reaction equation

HRID 654656 reaction equation
[CH:1]([NH:3][CH:4]([CH:11](O)[C:12](=[CH2:21])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].S(Br)([Br:25])=O.O>ClCCl>[CH:1]([NH:3][CH:4]([CH:11]=[C:12]([CH2:21][Br:25])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68176Thionyl bromideHCID 19886018HCID 19886018, compound

Product 1

HCID 54128616Diethyl 2-formylamino-4-bromomethyl-hept-3-ene-1,7-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.3 g (35.9 mmol) of diethyl 2-formylamino-3-hydroxy-4-methylene-heptane-1,7-dicarboxylate are dissolved in 100 ml of dichloromethane and 3.34 ml (43.1 mmol) of thionyl bromide are added dropwise to the solution at room temperature. After 1 hour, 10 ml of water are added and the batch is thoroughly stirred. The organic phase is separated, washed in succession with water, saturated potassium hydrogencarbonate solution and again with water, dried over magnesium sulfate and concentrated by evaporation, giving diethyl 2-formylamino-4-bromomethyl-hept-3-ene-1,7-dicarboxylate as a brownish oil.

Workup

  1. customThe organic phase is separated
  2. washwashed in succession with water, saturated potassium hydrogencarbonate solution and again with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-7d8b1cdb38614e1991771f76405344eb
Source dataset
uspto-grants-1992_07
Patent number
US05134134

Reaction notes

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