Triethylsilane → HCID 86688090, compound

HRID 407911Notes

Reaction equation

HRID 407911 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:15]1[C:19](=[O:20])[O:18][C:17]([CH3:22])([CH3:21])[O:16]1)[C:10](=[O:14])SCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(Cl)Cl.[Pd]>[CH2:1]([O:8][C@H:9]([C@@H:15]1[C:19](=[O:20])[O:18][C:17]([CH3:22])([CH3:21])[O:16]1)[CH:10]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 86688089HCID 86688089, compound

Product 1

HCID 86688090HCID 86688090, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(R)—S-Ethyl 2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (2.3 g, 7.09 mmol) was dissolved in CH2Cl2 (50 mL) and 10% palladium on carbon (0.377 g, 0.355 mmol) was added and stirred under nitrogen. Triethylsilane (1.70 mL, 10.6 mmol) was dissolved in CH2Cl2 (5 mL) and added dropwise. The reaction was allowed to stir overnight. The reaction was filtered, concentrated and purified over silica gel (5 to 10% EtOAc in hexanes) to afford a small amount of product and a large amount of starting material. The isolated starting material was subjected to the conditions described above and combined with the product isolated from the first batch to afford (R)-2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetaldehyde (750 mg, 2.84 mmol, 40% yield).

Workup

  1. additionadded dropwise
  2. stirringto stir overnight
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. custompurified over silica gel (5 to 10% EtOAc in hexanes)
  6. customto afford a small amount of product
  7. customisolated from the first batch

Sources & evidence

ORD record
ord-07159c9e6a41438e8c60d07e76a90821
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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