Triethylborane → HCID 19107712, compound

HRID 1197702Notes

Reaction equation

HRID 1197702 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][CH:12]([C:14](=[O:16])[CH3:15])[CH3:13].C(B(CC)CC)C.[O:24]([C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34]Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[CH3:11][CH:12]([C:14](=[O:16])[CH2:15][CH2:34][C:33]1[CH:36]=[CH:37][CH:38]=[C:31]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:32]=1)[CH3:13]

Participants

7

Reactant 4

HCID 7357TriethylboraneHCID 112513-Methyl-2-butanoneHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 19107712HCID 19107712, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of potassium bis (trimethylsilyl) amide (20.9 g, 0.105 mol) in 200 ml tetrahydrofuran at 0° C. was added 2-methyl-3-butanone (12 ml, 0.112 mol). After 15 minutes, triethylborane (100 ml of a 1.0M solution in hexanes) was added, followed by 24.8 g (0.094 mole) 3-phenoxybenzyl bromide. The mixture was stirred at 25° C. for 18 hours, poured into 300 ml water and extracted with ether. The organic phase was dried, filtered and concentrated, leaving a yellow oil. The crude ketone product was purified by chromatography over silica gel using 5% ethyl acetate in hexanes, producing 16.8 g of product, a light yellow oil.

Workup

  1. extractionextracted with ether
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customleaving a yellow oil
  6. customThe crude ketone product was purified by chromatography over silica gel using 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-55c9ca761ea840fc956179897bc564b6
Source dataset
uspto-grants-1994_01
Patent number
US05276205

Reaction notes

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