Hydrochloric Acid → 4-{[t-Butyl(diphenyl)silyl]oxy}-3-fluorophenol

HRID 1634734Notes

Reaction equation

HRID 1634734 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([F:29])[CH:6]=1)(=O)C.[OH-].[Na+].Cl>CO>[Si:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][C:7]=1[F:29])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 699857744-{[t-Butyl(diphenyl)silyl]oxy}-3-fluorophenyl acetate

Product 1

HCID 699876834-{[t-Butyl(diphenyl)silyl]oxy}-3-fluorophenolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{[t -Butyl(diphenyl)silyl]oxy}-3-fluorophenyl acetate (5.28 g, 12.92 mmol) was dissolved in methanol (100 mL). 1N NaOH (15.5 mL) was added. The solution was stirred for 30 minutes at ambient temperature. 1N HCl (16 mL) was added. The solvent was removed in vacuo and the solid partitioned between dichloromethane and water. The aqueous phase was washed with dichloromethane. The organic layers were combined and the solvent dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo to yield crude title compound (4.5 g, 12.28 mmol).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid partitioned between dichloromethane and water
  3. washThe aqueous phase was washed with dichloromethane
  4. dry with materialthe solvent dried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4e14128c55344091b621e2ece53f2106
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…