tert-Butyldimethylsilyl chloride → N,N-diethyl-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-(trifluoromethoxy)benzamide

HRID 1296275Notes

Reaction equation

HRID 1296275 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[O:12][C:13]([F:16])([F:15])[F:14])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>CN(C=O)C>[CH2:18]([N:3]([CH2:1][CH3:2])[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([O:11][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:7][C:6]=1[O:12][C:13]([F:14])([F:16])[F:15])[CH3:19]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 68687198N,N-diethyl-4-hydroxy-2-(trifluoromethoxy)benzamide

Product 1

HCID 68690714N,N-diethyl-4-[(1,1-dimethylethyl)dimethylsilyl]oxy-2-(trifluoromethoxy)benzamideYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of N,N-diethyl-4-hydroxy-2-(trifluormethoxy)benzamide (1876 mg, 6.8 mmol) and diisopropylethylamine (1747 mg, 13.5 mmol) in dry DMF (60 mL) was added chloro(1,1-dimethylethyl)dimethylsilane (1123 mg, 7.5 mmol). The reaction was stirred for 16 h and then quenched with 1M HCl. The reaction was extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pale yellow oil. The oil was purified by flash chromatography (silica gel, 0–40% EtOAc in hexanes) to give 1941 mg of the desired product as a colorless oil. MS (ESI) 392 (M+H).

Workup

  1. customquenched with 1M HCl
  2. extractionThe reaction was extracted with EtOAc (3×50 mL)
  3. dry with materialdried over Na2SO4
  4. customThe oil was purified by flash chromatography (silica gel, 0–40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-24fdbc3f07004d29bddb7c83f2c0cb3d
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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