Triethylamine → HCID 86722542, compound

HRID 1395924Notes

Reaction equation

HRID 1395924 reaction equation
[CH3:1][C:2]([OH:15])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:3].C(N(CC)CC)C.[Br:23][CH:24]([CH3:28])[C:25](Br)=[O:26]>C1(C)C=CC=CC=1>[Br:23][CH:24]([CH3:28])[C:25]([O:15][C:2]([CH3:1])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:3])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 10867656HCID 10867656, compound

Product 1

HCID 86722542HCID 86722542, compoundYield 61.27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
57.5 °C

Procedure

To a stirred solution of 2-methyltridecan-2-ol 73 (5 g, 23.4 mmol) in Toluene (50 mL) was added triethylamine (3.29 mL, 23.4 mmol)) and followed by 2-bromopropionyl bromide 58 (5.11 g, 23.7 mmol) at 5-10° C. The reaction mixture was stirred for 3 hours at 55-60° C.; 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 74 (5 g, yield: 61.27%) 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-613b8f625c524b7da8c537f18eaf0267
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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