Hydrochloric Acid → 5-((3-(((Tert-butyldiphenylsilyl)oxy)methyl)phenyl) (cyclopropyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1049406Notes

Reaction equation

HRID 1049406 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:34]=[CH:35][CH:36]=1)[CH:23]=[C:24]1[C:29](=[O:30])[O:28][C:27]([CH3:32])([CH3:31])[O:26][C:25]1=[O:33])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:37]1([Mg]Br)[CH2:39][CH2:38]1.Cl.O>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:23]([CH:37]2[CH2:39][CH2:38]2)[CH:24]2[C:25](=[O:33])[O:26][C:27]([CH3:31])([CH3:32])[O:28][C:29]2=[O:30])[CH:34]=[CH:35][CH:36]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1317360095-(3-(((Tert-butyldiphenylsilyl)oxy)methyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418630HCID 178418630, compound

Product 1

HCID 1317360105-((3-(((Tert-butyldiphenylsilyl)oxy)methyl)phenyl) (cyclopropyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, to a solution of 5-(3-(((tert-butyldiphenylsilyl)oxy)methyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (6.39 g) in THF (85 mL) was added dropwise a 0.70 M solution of cyclopropylmagnesium bromide in THF (54.7 mL) at 0° C. over 15 min, and the mixture was stirred at 0° C. for 5.5 hr. 0.50N Hydrochloric acid (300 mL) was added dropwise at 0° C., and water was further added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.05 g) as a colorless oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-82ab68b0f790407fb538b6991f524a33
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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