Chlorotrimethylsilane → HCID 58292869, compound

HRID 1798074Notes

Reaction equation

HRID 1798074 reaction equation
C[Si](Cl)(C)C.Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:13]([O:20][C:21]1[CH:28]=[C:27]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[CH:26]=[C:25]([B:36]2CC(C)(C)C(C)(C)C2)[C:22]=1[CH:23]=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C[O:48]CC1>[Zn]>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][CH:23]1[O:24][B:36]([OH:48])[C:25]2[CH:26]=[C:27]([O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)[CH:28]=[C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:22]1=2)[CH3:12]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7748Ethyl bromoacetateHCID 8028Tetrahydrofuran2×HCID 87325722HCID 87325722, compound

Product 1

HCID 58292869HCID 58292869, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst2×

Conditions

Temperature
40 °C

Procedure

To a suspension of powdered zinc dust (3.3 g, 51 mmol) in THF (20 mL) was added trimethylsilyl chloride at room temperature. The reaction mixture was stirred at 40° C. for 20 min and ethyl bromoacetate (5.59 g, 33.0 mmol) was slowly added, the reaction mixture was stirred at 40° C. for an additional 30 min. To a solution of 2-(benzyloxy)-4-(tetrahydro-2H-pyran-2-yloxy)-6-(3,3,4,4-tetramethylborol-1-yl)benzaldehyde (2.8 g, 6.4 mmol) in THF (15 mL) was added dropwise the above prepared zinc reagent at −78° C. The reaction mixture was stirred at room temperature for 1 h and quenched by saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a light yellow oil (1.3 g, yield: 48%).

Workup

  1. stirringthe reaction mixture was stirred at 40° C. for an additional 30 min
  2. stirringThe reaction mixture was stirred at room temperature for 1 h
  3. customquenched by saturated aqueous NH4Cl
  4. extractionThe resulting mixture was extracted with EtOAc (3×25 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d461f1e0ee849c5bd448f70b616a02f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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