Potassium Hydroxide → HCID 69987236, compound

HRID 1634730Notes

Reaction equation

HRID 1634730 reaction equation
C([O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[Cl:28])=O.[OH-].[K+]>CO>[Si:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([OH:3])=[C:5]([Cl:28])[CH:6]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 88088784HCID 88088784, compound

Product 1

HCID 69987236HCID 69987236, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{[t-butyl(diphenyl)silyl]oxy}-2-chlorophenyl formate (9.42 g, 22.4 mmol) was dissolved in methanol (50 mL). 10% KOH (15 mL) was added. The solution was stirred for 30 minutes at ambient temperature. The solvent was removed in vacuo and the solid partitioned between ethyl acetate and water. The aqueous phase was acidified with HCl and extracted three times with ethyl acetate. 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 (8.04 g, 21 mmol).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid partitioned between ethyl acetate and water
  3. extractionextracted three times with ethyl acetate
  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-5cae2acc4efa47c292fa41164917b3a1
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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