Hydrochloric Acid → HCID 130823, compound

HRID 1090427Notes

Reaction equation

HRID 1090427 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([Si:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1.[CH:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=1)=O.[OH-].[Na+].Cl>C1COCC1.O>[CH3:11][Si:9]([CH3:10])([CH3:12])[C:7]1[CH:6]=[C:5]([C:13](=[O:15])[CH:14]=[CH:18][C:20]2[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[CH:4]=[C:3]([Si:2]([CH3:16])([CH3:1])[CH3:17])[CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 15294Methyl 4-FormylbenzoateHCID 128849103',5'-Bis(trimethylsilyl)acetophenone

Product 1

HCID 130823HCID 130823, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, to a solution of 114 mg (0.43 mmol) of 3',5'-bis(trimethylsilyl)acetophenone and 70 mg (0.43 mmol) of methyl 4-formylbenzoate in 3 ml of THF was added a solution of 40 mg (1.00 mmol) of NaOH in 2 ml of H2O with stirring, and the mixture was stirred in an atmosphere of prepurified argon overnight. The reaction mixture was further added to 39 mg of NaOH, stirred for 2 days, and then the solution was adjusted with 2N-HCl to pH≤7 and extracted with ethyl acetate. The extract was dried and evaporated. The residue was purified by column chromatography using methylene chloride-methanol (10:1) as an eluant to give 112 mg of the desired compound (yield 66%), which was recrystallized from a mixture of ethyl acetate and n-hexane to give 98 mg of pale yellow prisms, m.p.194°-195.5° C. (yield 57%).

Workup

  1. stirringthe mixture was stirred in an atmosphere of prepurified argon overnight
  2. stirringstirred for 2 days
  3. extractionextracted with ethyl acetate
  4. customThe extract was dried
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e3ef1271621046c6a1ff88a1ca732533
Source dataset
uspto-grants-1992_01
Patent number
US05081271

Reaction notes

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