1,5-Hexadiene → HCID 21612924, compound

HRID 1682316Notes

Reaction equation

HRID 1682316 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:12][CH:13]=[O:14])[CH:5](O)[C:6](=[CH2:10])[CH2:7][CH:8]=[CH2:9].C=CCCC=C.S(Br)([Br:24])=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:12][CH:13]=[O:14])/[CH:5]=[C:6](/[CH2:10][Br:24])\[CH2:7][CH:8]=[CH2:9]

Participants

6

Reactant 4

HCID 115981,5-HexadieneHCID 68176Thionyl bromideHCID 516892Sodium BicarbonateHCID 21612914HCID 21612914, compound

Product 1

HCID 21612924HCID 21612924, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g of 2-formylamino-3-hydroxy-4-methylene-6-heptenoic acid methyl ester in 200 ml of dry tetrahydrofuran are cooled to -78°, and 20 ml of 1,5-hexadiene are added thereto. 9 ml of thionyl bromide are added slowly dropwise in such a manner that the reaction temperature does not exceed -50°. When the addition is complete, the reaction solution is heated to 0° within a period of approximately 3 hours and is stirred at that temperature for 3 hours. The solution is then poured onto 300 ml of a cold (5°-10°) saturated sodium bicarbonate solution and extracted with diethyl ether. The organic extracts are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation in vacuo. Purification by column chromatography (silica gel, ethyl acetate/hexane 1:1) yields E-2-formylamino-4-bromomethyl-3,6-heptadienoic acid methyl ester in the form of a colourless oil, 1H-NMR (CDCl3): 3.20 (d, 2H, C(5 )-H); 4.00 (s, 2H, CH2Br).

Workup

  1. customdoes not exceed -50°
  2. additionWhen the addition
  3. temperaturethe reaction solution is heated to 0° within a period of approximately 3 hours
  4. extractionextracted with diethyl ether
  5. washThe organic extracts are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation in vacuo
  8. customPurification by column chromatography (silica gel, ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-fb876473086e4b5393017cc1bf9efd92
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

Loading…