Toluene → HCID 44464035, compound

HRID 2065482Notes

Reaction equation

HRID 2065482 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O-:9])=[CH2:2].[K+].[OH-].[K+].C1(C)C=CC=CC=1.Br[CH:21]([CH3:29])[C:22]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:24]1([C:22](=[O:23])[CH:21]([O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[CH2:2])[CH3:29])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 5666731-(2-Bromopropanoyl)pyrrolidineHCID 66644874HCID 66644874, compound

Product 1

HCID 44464035HCID 44464035, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 6.35 g (40.1 mmol) potassium 2-vinylphenolate in 110 mL of water (pH adjusted to 14 by addition of KOH) under argon was added 150 mL of toluene, 0.65 g (2.0 mmol) of tetrabutylammonium bromide and 11.54 g (50.16 mmol) of 2-bromo-1-pyrrolidin-1-yl-propan-1-one. The two-phase mixture was stirred vigorously over night at 45° C. After this time the organic phase was removed, washed with water, 4 M sodium hydroxide aqueous solution, 1 M hydrochloric acid solution and water, dried (Na2SO4), and evaporated to dryness. Crystallization of the residue from warm heptane (200 mL) afforded the title compound as a white powder (7.0 g, 70.5% yield): MP 85-86° C., MS: 246.1496 (M+H)+, 268.1317 (M+Na)+.

Workup

  1. customAfter this time the organic phase was removed
  2. washwashed with water, 4 M sodium hydroxide aqueous solution, 1 M hydrochloric acid solution and water
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customCrystallization of the residue
  6. temperaturefrom warm heptane (200 mL)

Sources & evidence

ORD record
ord-6c88dbc76db9493c96277a4b99a819dc
Source dataset
uspto-grants-2012_10
Patent number
US08288534B2

Reaction notes

Loading…