2,4-Dichlorobenzaldehyde → HCID 11591151, compound

HRID 1444794Notes

Reaction equation

HRID 1444794 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:31][C:32]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:33]=1[CH:34]=[O:35]>C1COCC1>[Cl:31][C:32]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:33]=1[CH:34]([OH:35])[CH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][S:13]([C:16]([F:18])([F:19])[F:17])(=[O:15])=[O:14])=[CH:9][CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1

Participants

5

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 59776431HCID 59776431, compound

Product 1

HCID 11591151HCID 11591151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Trifluoro-methanesulfonic acid 4-methyl-2-oxo-2H-chromen-7-yl ester (340 mg, 1.1 mmol) in dry THF (8 mL0 at −20° C. was added drop wise 1.0 M LiHMDS solution in THF (1.2 mL). After 30 minutes 2,4-dichloro-benzaldehyde (130 μL) was added slowly into the reaction mixture and the reaction-mixture was stirred for 1 hour. The reaction mixture was 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, concentrated and purified on silica gel eluted with 30% ethyl acetate in hexanes to yield trifluoro-methanesulfonic acid 4-[2-(2,4-dichloro-phenyl)-2-hydroxy-ethyl]-2-oxo-2H-chromen-7-yl ester as a light yellow solid.

Workup

  1. customThe reaction mixture was 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-4811488636004acda8361f8bb3aaa517
Source dataset
uspto-grants-2010_02
Patent number
US07662975B2

Reaction notes

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