1,5-Hexadiene → HCID 21612924, compound

HRID 728881Notes

Reaction equation

HRID 728881 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 washedwith 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. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated by evaporation in vacuo
  7. customPurification by column chromatography (silica gel, ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-089f2ffbeaf74737831d6cf2507cf458
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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