1,6-Dibromohexane → Methyl 6-bromohexyloxy-2-methylpropionate

HRID 1796352Notes

Reaction equation

HRID 1796352 reaction equation
[H-].[Na+].[OH:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>CN(C)C=O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 75024Methyl alpha-hydroxyisobutyrate

Product 1

HCID 21866674Methyl 6-bromohexyloxy-2-methylpropionateYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 120 ml of dry N,N-dimethylformamide, 4.0 g of 60% sodium hydride was added. To the mixture was added dropwise 11.81 g of methyl 2-hydroxyisobutyrate with stirring under ice-cooling, and stirred for 10 minutes. Then, 122 g of 1,6-dibromohexane was added and stirred for 15 hours at room temperature. The reaction solution was poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=20:1) to provide 6.25 g of the objective compound as yellowish oil.

Workup

  1. temperaturecooling
  2. stirringstirred for 10 minutes
  3. stirringstirred for 15 hours at room temperature
  4. additionThe reaction solution was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-340e8f3379044c789269bed7c076cc8b
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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