Ethyl Acetate → HCID 57847746, compound

HRID 736007Notes

Reaction equation

HRID 736007 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C(OCC)(=O)C>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 21642BromopinacoloneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 20743446HCID 20743446, compound

Product 1

HCID 57847746HCID 57847746, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-fluoropyridin-4-yl)-1-phenylethanone (450 mg, 2.1 mmol) in dry THF (10 mL) at 0° C. was added a solution of sodium bis(trimethylsilyl)amide (2.1 mL, 1M). After 10 min. 1-bromopinacolone (309 μL, 2.3 mmol) was added dropwise and the solution stirred for 2 h. The solution was poured into ethyl acetate (25 mL) and H2O (25 mL) and the layers allowed to separate. The organic layer was collected and the aqueous layer extracted with ethyl acetate (30 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4) and concentrated. The product was purified by flash chromatography using EtOAc-Pet. spirit (20:80) as eluant to give the pure product as a pale yellow oil (574 mg, 87%).

Workup

  1. customto separate
  2. customThe organic layer was collected
  3. extractionthe aqueous layer extracted with ethyl acetate (30 mL)
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-fe84fde5652b4341a8cff577e792bc1e
Source dataset
uspto-grants-2009_09
Patent number
US07593820B2

Reaction notes

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