Lithium Bromide → HCID 53744629, compound

HRID 223675Notes

Reaction equation

HRID 223675 reaction equation
[CH:1]([O:5][C:6](=[O:26])[CH2:7][CH:8]([CH3:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O)([CH2:3][CH3:4])[CH3:2].[Br-:27].[Li+]>CC(C)=O>[CH:1]([O:5][C:6](=[O:26])[CH2:7][CH:8]([CH3:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Br:27])([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 53673877HCID 53673877, compound

Product 1

HCID 53744629HCID 53744629, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 337 mg of 3-methyl-8-(p-toluenesulphonyloxy)octanoic acid sec-butyl ester (prepared as described hereafter), 5 ml of acetone and 156 mg of lithium bromide was stirred at 70° C. for 1.5 hours. After evaporation under reduced pressure, the residue was dissolved in ethyl acetate, washed with water, a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of methylene chloride and cyclohexane (1:1) as eluent to give 204 mg of the title compound having the following physical characteristics:

Workup

  1. customAfter evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of methylene chloride and cyclohexane (1:1) as eluent

Sources & evidence

ORD record
ord-50b0194827904824baf7383b74dfb459
Source dataset
uspto-grants-1982_10
Patent number
US04355170

Reaction notes

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