Sodium Bicarbonate → HCID 86590125, compound

HRID 1884917Notes

Reaction equation

HRID 1884917 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH3:30])[C:9]=1[C:10]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH3:20])=[C:14]([O:21][CH3:22])[C:13]=1[O:23][CH3:24])=[O:11].C([O-])(O)=O.[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH3:30])[C:9]=1[CH:10]([OH:11])[C:12]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH3:20])=[C:14]([O:21][CH3:22])[C:13]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11417330HCID 11417330, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86590125HCID 86590125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under protective gas conditions, at about −78° C., 1 ml of a 1-molar solution of LiAlH4 in tetrahydrofuran was added dropwise to a solution of 0.37 g of 2,5-dichloro-6,6′-dimethyl-2′, 3′, 4′-trimethoxybenzophenone in 20 ml of anhydrous tetrahydrofuran, and the mixture was stirred for about 1 hour. At 20-25° C., sat. NaHCO3 solution was added to the reaction solution, the solution was extracted with ethyl acetate and the organic phase was washed with water and sat. NaCl solution and dried, and the solvent was then distilled off. The residue gave, after purification by column chromatography (mobile phase: ethyl acetate/cyclohexane 1:9), 150 mg of the title compound as a yellow viscous oil.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washthe organic phase was washed with water and sat. NaCl solution
  3. customdried
  4. distillationthe solvent was then distilled off
  5. customThe residue gave
  6. customafter purification by column chromatography (mobile phase: ethyl acetate/cyclohexane 1:9), 150 mg of the title compound as a yellow viscous oil

Sources & evidence

ORD record
ord-36847311ec9a451ea48f55015d3839f3
Source dataset
uspto-grants-2004_07
Patent number
US06767923B2

Reaction notes

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