Triethylamine → HCID 86722543, compound

HRID 1395926Notes

Reaction equation

HRID 1395926 reaction equation
[CH3:1][CH:2]([OH:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(N(CC)CC)C.[Br:22][C:23](C)([CH3:27])[C:24](Br)=[O:25]>C1(C)C=CC=CC=1>[Br:22][CH:23]([CH3:27])[C:24]([O:14][C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH2:1])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15449Tridecan-2-olHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 86722543HCID 86722543, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
57.5 °C

Procedure

To a stirred solution of tridecan-2-ol 68 (5 g, 24.9 mmol) in toluene (50 mL) was added triethylamine (3.5 mL, 27.45 mmol)) and followed by 2-bromo-2-methylpropionyl bromide 97 (6.31 g, 27.45 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C., and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated. The organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 98 (8.1 g, yield: 96%) as a liquid.

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate solution
  2. stirringstirred for 15 minutes at 25-35° C
  3. customThe aqueous and organic layers were separated
  4. washThe organic layer was washed with brine
  5. washthe combined organic layers were washed with brine solution
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7720d39a9e1b424fa867ae05d833f18e
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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