Methyl 4-methylbenzoate → HCID 67246324, compound

HRID 1190860Notes

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>[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

Conditions

Temperature: 5 °C

Procedure

Under a stream of nitrogen, 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. 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 room temperature for 2 hours 30 minutes and then cooled to 5° C., followed by gradual addition of 20 mL of water. The medium is then diluted with 200 mL of ethyl acetate and 200 mL of water. The organic phase is separated out, dried over sodium sulfate and filtered. 5 g of silica are then added to the filtrate, which is then concentrated under reduced pressure. The powder obtained is used as a solid deposit for a chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (95/5) to give 1.03 g (61%) of compound in the form of a yellow powder.

Workup

additionAfter addition
temperaturecooled to 5° C.
customThe organic phase is separated out
dry with materialdried over sodium sulfate
filtrationfiltered
addition5 g of silica are then added to the filtrate, which
concentrationis then concentrated under reduced pressure
customThe powder obtained
washeluting with a mixture of cyclohexane and ethyl acetate (95/5)

Sources & evidence

ORD record: ord-5b0701c13a0f47a68e9e8ea07e105647
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680096B2

Reaction notes

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