Triethylamine → [1-(4-Bromo-phenyl)-cyclobutoxy]-tert-butyl-dimethyl-silane

HRID 9234

Reaction equation

HRID 9234 reaction equation
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2(O)[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 120954191-(4-Bromophenyl)cyclobutanol

Product 1

HCID 21985972[1-(4-Bromo-phenyl)-cyclobutoxy]-tert-butyl-dimethyl-silaneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TBSOTf (360 μL, 1.57 mmol) was added to a 0° C. solution of 3-1 (235 mg, 1.04 mmol) and triethylamine (450 μL, 3.23 mmol) in dichloromethane (3 mL). The reaction was allowed to warm to room temperature and after 1 h, saturated NaHCO3 solution was added. The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (hexanes) gave 3-2 (329 mg, 93%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. washthe combined ethyl acetate solution was washed with brine
  3. dry with materialThe solution was then dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-3369d74bfe9e4f18bb09dcce8d3f401e
Source dataset
uspto-grants-2006_08
Patent number
US07091231B2

Linked notes

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