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

HRID 857201Notes

Reaction equation

HRID 857201 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-4ff33e458f294d96ad63cde91b3041c6
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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