Triethylsilane → HCID 24864236, compound

HRID 1098681Notes

Reaction equation

HRID 1098681 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>[Pd].C(Cl)Cl>[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 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of (R)—S-ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (1.9 g, 8.7 mmol), 10% palladium on carbon (470 mg), and CH2Cl2 (20 mL) under N2, at 25° C., was added triethylsilane (2.08 mL, 13.0 mmol) dropwise over 10 minutes. The mixture was stirred at 25° C. for 1 hour. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to give the desired aldehyde as a clear oil (1.2 g, 87%). 1H-NMR (400 MHz, CDCl3) δ 9.70 (s, 1H), 4.72 (q, J=3.5 Hz, 1H), 3.10-3.01 (m, 1H), 2.93-2.84 (m, 1H), 1.56 (s, 3H), 1.51 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ec8c3b710d724332999d9775c23fe7f7
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

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