Imidazole → (R)-tert-Butyl(2-(5-fluoro-2-methoxyphenyl)propoxy)dimethylsilane

HRID 708889Notes

Reaction equation

HRID 708889 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[F:14][C:15]1[CH:16]=[CH:17][C:18]([O:25][CH3:26])=[C:19]([C@@H:21]([CH3:24])[CH2:22][OH:23])[CH:20]=1>C(Cl)Cl.CCOC(C)=O>[C:6]([Si:10]([O:23][CH2:22][C@@H:21]([C:19]1[CH:20]=[C:15]([F:14])[CH:16]=[CH:17][C:18]=1[O:25][CH3:26])[CH3:24])([CH3:13])[CH3:12])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 93691874(2R)-2-(5-fluoro-2-methoxyphenyl)propan-1-ol

Product 1

HCID 123598626(R)-tert-Butyl(2-(5-fluoro-2-methoxyphenyl)propoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (3.55 g, 52.1 mmol) and tert-butyldimethylchlorosilane (10.21 g, 33.9 mmol) were added to a solution of 25A (4.8 g, 26.1 mmol) in CH2Cl2 (125 mL) and stirred overnight at rt. The reaction mixture was diluted with EtOAc (150 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (loading in chloroform, 0% to 20% ethyl acetate in hexane) to yield 25B as a clear oil.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (loading in chloroform, 0% to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d76ad1baa0b34cdaa24db2a872ef1d94
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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