Benzoyl chloride, 3-chloro- → HCID 86610814, compound

HRID 564037Notes

Reaction equation

HRID 564037 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[O:5][C:4](=[O:14])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30]>C1COCC1>[Cl:25][C:26]1[CH:27]=[C:28]([C:29](=[O:30])[CH2:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=3)[O:5][C:4](=[O:14])[CH:3]=2)[CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 2733832Lithium HexamethyldisilazideHCID 86610812HCID 86610812, compound

Product 1

HCID 86610814HCID 86610814, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-2-oxo-2H-chromene-6-carbonitrile (180 mg, 0.92 mmol) in dry THF (33 mL) at −20° C. was added drop wise 1.0 M LiHMDS solution in THF (1.6 mL). After 30 minutes 3-chlorobenzoylchloride (200 mg) was added into the reaction mixture and the reaction mixture was stirred for 1 hour. The reaction mixture was then quenched with saturated aqueous ammonium chloride (15 mL) and extracted with ethyl acetate (50 mL). The organic layer was separated and dried over sodium sulfate, then concentrated and purified on silica gel eluted with 30%-60% ethyl acetate in hexanes to yield 4-[2-(3-chloro-phenyl)-2-oxo-ethyl]-2-oxo-2H-chromene-6-carbonitrile as a white solid.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride (15 mL)
  2. extractionextracted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified on silica gel
  7. washeluted with 30%-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-296bbb343a384aaa9a9a4bba56b87013
Source dataset
uspto-grants-2011_11
Patent number
US08067619B2

Reaction notes

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