2,4-Dichlorobenzaldehyde → HCID 86610809, compound

HRID 564029Notes

Reaction equation

HRID 564029 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:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>C1COCC1>[Cl:25][C:26]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:27]=1[CH:28]([OH:29])[CH2:1][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

Participants

5

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 15015001HCID 15015001, compound

Product 1

HCID 86610809HCID 86610809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methyl-2-oxo-2H-chromene-7-carbonitrile (76 mg, 0.427 mmol) in dry THF (4 mL) at −20° C. was added drop wise 1.0 M LiHMDS solution in THF (0.52 mL). After 30 minutes 2,4-dichloro-benzaldehyde (60 μL) was added slowly into the reaction mixture and then stirred for 1 hour. The reaction mixture was then quenched with saturated aqueous ammonium chloride (2 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 4-[2-(2,4-dichloro-phenyl)-2-hydroxy-ethyl]-2-oxo-2H-chromene-7-carbonitrile as a yellow solid.

Workup

  1. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride (2 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-698b8dd3e3d646b9a73ff65cf8d6dfc3
Source dataset
uspto-grants-2011_11
Patent number
US08067619B2

Reaction notes

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