Triethylamine → Tert-butyl(2-fluoro-5-methoxyphenoxy)dimethylsilane

HRID 2089676Notes

Reaction equation

HRID 2089676 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[OH-].[Na+]>O1CCCC1.CCCCCCC>[C:21]([Si:18]([O:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1])([CH3:20])[CH3:19])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 141189572-Fluoro-5-methoxyphenol

Product 1

HCID 67469961Tert-butyl(2-fluoro-5-methoxyphenoxy)dimethylsilaneYield 94.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8900HeptaneSolvent

Procedure

To a flask, 2-fluoro-5-methoxyphenol (6.00 g, 42 mmol), triethylamine (5.77 g, 57 mmol), and tetrahydrofuran (36.0 mL) were added, and the resulting mixture was cooled in an ice water bath under nitrogen atmosphere. To the solution, a solution of tert-butyldimethylsilyl chloride (6.89 g, 44 mmol) in tetrahydrofuran (30.0 mL) was added dropwise, and the resulting mixture was stirred overnight at room temperature. To the reaction mixture, heptane and a 2 N aqueous sodium hydroxide solution were added, and the resulting mixture was extracted. The organic layer was washed with water, and concentrated under reduced pressure to obtain the captioned compound (10.2 g) as a light brownish-red oil.

Workup

  1. temperaturethe resulting mixture was cooled in an ice water bath under nitrogen atmosphere
  2. extractionthe resulting mixture was extracted
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33c135b237134441b736a2e66c26860e
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

Loading…