Methyl 4-methylbenzoate → HCID 67246324, compound

HRID 1036653Notes

Reaction equation

HRID 1036653 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[CH3:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=1.C[Si](C)(C)N[Si](C)(C)C.[Li]>O1CCCC1.C(OCC)(=O)C.O.C1CCCCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:14]([C:13]2[CH:18]=[CH:19][C:10]([CH3:9])=[CH:11][CH:12]=2)=[O:15])[CH:3]=1

Participants

8

Reactant 3

HCID 7455Methyl 4-methylbenzoateHCID 27628354-Bromo-2-methylpyridineHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 67246324HCID 67246324, compoundYield 61.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
5 °C

Procedure

1 g (5.81 mmol) of 4-bromo-2-methylpyridine and 1.75 g (11.60 mmol) of methyl 4-methylbenzoate are placed in a round-bottomed flask and dissolved in 30 ml of anhydrous tetrahydrofuran under a stream of nitrogen. The solution is cooled to 5° C. and 14 ml (14 mmol) of a lithium hexamethyldisilazane solution (1M in tetrahydrofuran) are added dropwise. After addition, the mixture is stirred at ambient temperature for 2 h 30 and then cooled to 5° C., before gradually adding 20 ml of water. The medium is subsequently diluted with 200 ml of ethyl acetate and 200 ml of water. The organic phase is separated, dried over sodium sulphate and filtered. 5 g of silica are subsequently added to the filtrate before concentrating it under reduced pressure. The powder obtained is used as solid deposit for chromatography on silica gel with a mixture of cyclohexane and ethyl acetate (95/5) as eluent. 1.03 g (61%) of compound are obtained in the form of a yellow powder.

Workup

  1. additionAfter addition
  2. temperaturecooled to 5° C.
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. addition5 g of silica are subsequently added to the filtrate
  7. concentrationbefore concentrating it under reduced pressure
  8. customThe powder obtained

Sources & evidence

ORD record
ord-9248cbbdcad4484eb8849475d0b3a51c
Source dataset
uspto-grants-2013_10
Patent number
US08546424B2

Reaction notes

Loading…