Pyridine → HCID 19886002, compound

HRID 654924Notes

Reaction equation

HRID 654924 reaction equation
[OH:1][CH:2]([C:15]1[CH:19]([O:20][CH3:21])[O:18][C:17](=[O:22])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Br:23]Br.N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Br:23][C:16]1[C:17](=[O:22])[O:18][CH:19]([O:20][CH3:21])[C:15]=1[CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 19885950HCID 19885950, compound

Product 1

HCID 19886002HCID 19886002, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture of 0.3 g. of 4-(1-hydroxytridecyl)-5-methoxy-2(5H)-furanone and 0.5 ml of carbon tetrachloride is cooled to 0° and 0.55 ml of a 3.1M solution of bromine in carbon tetrachloride is added dropwise over 15 minutes. Two drops of glacial acetic acid are added and the mixture is allowed to warm to room temperature. The reaction is monitored by TLC. After one hour, the mixture is cooled to 0° and 25 ml of pyridine is added over 5 minutes. The mixture is stirred for one hour, filtered to remove pyridine hydrobromide and solvent removed to give a residue which is purified by flash chromatography to give 3-bromo-4-(1-hydroxytridecyl)-5-methoxy-2(5H)-furanone.

Workup

  1. additionA mixture of 0.3 g
  2. temperaturethe mixture is cooled to 0°
  3. filtrationfiltered
  4. customto remove pyridine hydrobromide and solvent
  5. customremoved
  6. customto give a residue which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-5d3d429c9d514d7788fbeddb31465d27
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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