Triethylsilane → HCID 24864236, compound

HRID 407872Notes

Reaction equation

HRID 407872 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][C:8](=[O:12])SCC)[C:4](=[O:13])[O:3]1.C([SiH](CC)CC)C>C(Cl)Cl.[Pd]>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][CH:8]=[O:12])[C:4](=[O:13])[O:3]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 53627664HCID 53627664, compound

Product 1

HCID 24864236HCID 24864236, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(R)—S-Ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (22.5 g, 103 mmol) was dissolved in CH2Cl2 (500 mL), purged with nitrogen and 10% palladium on carbon (2.19 g, 2.06 mmol) was added and triethylsilane (24.7 mL, 155 mmol) was dissolved in CH2Cl2 (20 mL) and added dropwise through an addition funnel over 30 minutes and stirred at ambient temperature overnight under nitrogen. The reaction was filtered through celite, concentrated and purified over silica gel (10 to 40% EtOAc in hexanes) to afford (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetaldehyde (16 g, 101 mmol, 98.1% yield) as a clear colorless oil.

Workup

  1. additionwas added
  2. additionadded dropwise through an addition funnel over 30 minutes
  3. filtrationThe reaction was filtered through celite,
  4. concentrationconcentrated
  5. custompurified over silica gel (10 to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5579effdb07540a5849ba76d8695aa48
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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