4-Chlorobenzoyl chloride → HCID 86640086, compound

HRID 564024Notes

Reaction equation

HRID 564024 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][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:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>C1COCC1>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([C:3]2[C:4](=[O:14])[O:5][C:6]3[C:11]([C:2]=2[CH3:1])=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=3)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 15015001HCID 15015001, compound

Product 1

HCID 86640086HCID 86640086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-2-oxo-2H-chromene-7-carbonitrile (170 mg, 0.918 mmol) in dry THF (5 mL) at −20° C. was added drop wise 1.0 M LiHMDS solution in THF (1 mL). After 30 minutes 4-chloro-benzoyl chloride (160 μL) was added slowly and the reaction mixture was stirred for 1 hour. The reaction mixture was then quenched with saturated aqueous ammonium chloride (10 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% ethyl acetate in hexanes to yield the title compounds as a white foam and a white solid, respectively.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride (10 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% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-56ed573ee7c54fb8a680c6b23f220fa0
Source dataset
uspto-grants-2011_11
Patent number
US08067619B2

Reaction notes

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