Acetone → HCID 71089542, compound

HRID 716807Notes

Reaction equation

HRID 716807 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[CH2:16][OH:17].C([Li])CCC.[CH3:23][C:24]([CH3:26])=[O:25]>CCCCCC.C1COCC1>[Si:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:16][OH:17])=[C:2]([C:24]([OH:25])([CH3:26])[CH3:23])[CH:7]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 180AcetoneHCID 71089526HCID 71089526, compound2×HCID 178418339Butyllithium

Product 1

HCID 71089542HCID 71089542, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent3×

Procedure

To a solution of [2-bromo-4-[tert-butyl(dimethyl)silyl]oxy-phenyl]methanol (Intermediate 9, 500 mg, 1.5758 mmol) in dry hexane (8 mL) and THF (2 mL) at −15° C. butyllithium 1.6M in hexane (2.17 ml, 3.467 mmol) was slowly added (10 min) and the reaction mixture was stirred at the same temperature for 2 hours. Then a solution of acetone (118.98 mg, 2.0486 mmol) in dry hexane (1 ml) was added at −15° C. and the reaction mixture stirred at the same temperature for additional 1 hour. The reaction was quenched with an aqueous saturated solution of ammonium chloride and extracted with ethyl acetate (100 ml). The organic layer was washed with brine, dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (Biotage system) using a SNAP 50 g as column and cyclohexane/ethyl acetate from 100:0 to 60:40 as eluent in 12 column volumes, to give the title compound (240 mg) as a colourless oil.

Workup

  1. stirringthe reaction mixture stirred at the same temperature for additional 1 hour
  2. customThe reaction was quenched with an aqueous saturated solution of ammonium chloride
  3. extractionextracted with ethyl acetate (100 ml)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography on silica gel (Biotage system)

Sources & evidence

ORD record
ord-26fbdb9cd4fb447493fd60b7cae6525f
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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