Propyl chloroformate → HCID 54711862, compound

HRID 634849Notes

Reaction equation

HRID 634849 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11].OC1C=C(C)OC(=O)C=1.ClC(OCCC)=O.[Br:32]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>II.C(Cl)(Cl)Cl>[Br:32][C:7]1[C:2]([OH:1])=[C:3]([C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11])[C:4](=[O:9])[O:5][C:6]=1[CH3:8]

Participants

8

Reactant 5

HCID 7998Propyl chloroformateHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 546757574-Hydroxy-6-methyl-2-pyroneHCID 54724707HCID 54724707, compound

Product 1

HCID 54711862HCID 54711862, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 6212ChloroformSolvent2×

Conditions

Temperature
5 °C

Procedure

A chloroform (100 ml) solution of 4-hydroxy-6-methyl-3-propoxycarbonyl-2-pyrone (6.0 g, 28.3 mmol), synthesized from 4-hydroxy-6-methyl-2-pyrone and propyl chloroformate, was ice cooled, and a chloroform (100 ml) solution of bromine (4.0 ml, 78 mmol) and iodine (140 mg, 0.55 mmol) slowly added dropwise. After stirring for 7 days at 5° C., an aqueous sodium thiosulphate solution was added and separation performed. After drying and concentrating, crystallization was performed from ethanol and there was obtained the bromo-derivative, 5-bromo-4-hydroxy-6-methyl-3-propoxycarbonyl-2-pyrone (3.36 g, 41%), as white crystals.

Workup

  1. temperaturecooled
  2. customseparation
  3. customAfter drying
  4. concentrationconcentrating
  5. customcrystallization

Sources & evidence

ORD record
ord-6b8a8e203c6e4763a7336f04fe525e38
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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