4-Methylbenzoyl Chloride → HCID 67434527, compound

HRID 1430597Notes

Reaction equation

HRID 1430597 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C1COCC1>[O:30]=[C:29]([C:28]1[CH:32]=[CH:33][C:25]([CH3:24])=[CH:26][CH:27]=1)[CH:7]([C:3]1[CH:2]=[C:1]([CH3:13])[CH:6]=[CH:5][CH:4]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 96574Ethyl m-tolylacetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 67434527HCID 67434527, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) solution of ethyl 2-m-tolylacetate (1.697 g, 9.52 mmol) in THF (10.58 mL) was added LiHMDS (9.52 mL, 9.52 mmol). The reaction was stirred for 15 minutes and 4-methylbenzoyl chloride (1.546 g, 10 mmol) in THF (21.16 mL) was slowly added. The reaction was allowed to warm to room temperature over 2 h. The reaction was quenched with AcOH, diluted with water and extracted with EtOAc three times. The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow oil (2.213 g). 1H NMR (400 M Hz, CDCl3) δ ppm 1.24 (t, J=7.07 Hz, 3H), 2.33 (s, 3H), 2.37 (s, 3H), 4.15-4.28 (m, 2H), 5.54 (s, 1H), 7.10 (d, J=7.07 Hz, 1H), 7.16-7.25 (m, 5H), 7.85 (d, J=8.08 Hz, 2H).

Workup

  1. customThe reaction was quenched with AcOH
  2. additiondiluted with water
  3. extractionextracted with EtOAc three times
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f995c81efd04f09840b8cd6bb91a1fc
Source dataset
uspto-grants-2015_01
Patent number
US08940891B2

Reaction notes

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