Acetic Acid → HCID 88213798, compound

HRID 428810Notes

Reaction equation

HRID 428810 reaction equation
C[O-].[Na+].[CH3:4][Si:5]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1)([CH3:13])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[N:26](OCCC(C)C)=[O:27].C(O)(=O)C>CO>[CH3:4][Si:5]([CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22](=[N:26][OH:27])[C:23](=[O:25])[CH3:24])=[CH:20][CH:21]=1)([CH3:13])[C:6]1[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8053Isoamyl NitriteHCID 10942334Sodium MethoxideHCID 18359436HCID 18359436, compound

Product 1

HCID 88213798HCID 88213798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

28 ml of a 30% solution of sodium methanolate in methanol are added at room temperature to 31.6 g of 1-(4-[{dimethyl-(4-fluorophenyl)-silyl}methoxy]phenyl)-propan-2-one in 300 ml of methanol, and 27 ml of isopentyl nitrite are then added dropwise. The reaction mixture is stirred for a further hour and rendered neutral with acetic acid; the solvent is evaporated off in vacuo. 200 ml of ethyl acetate are added to the residue; the organic phase is washed with water and saturated sodium chloride solution and dried over sodium sulfate; the solvent is evaporated off in vacuo. Recrystallisation from diethyl ether/hexane yields the title product having a melting point of 115-117° C.

Workup

  1. additionare then added dropwise
  2. customthe solvent is evaporated off in vacuo
  3. addition200 ml of ethyl acetate are added to the residue
  4. washthe organic phase is washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated off in vacuo
  7. customRecrystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-edd9d9b6d91448b890e8a25a626d9dbf
Source dataset
uspto-grants-2001_11
Patent number
US06313344B1

Reaction notes

Loading…