2,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctane → HCID 14638051, compound

HRID 521302

Reaction equation

HRID 521302 reaction equation
C[Si](C)(C)[O:3][CH2:4][CH2:5][O:6][Si](C)(C)C.[CH3:13][C:14]([CH3:23])([CH2:19][N+:20]([O-:22])=[O:21])[CH2:15][C:16](=O)[CH3:17]>ClCCl.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>[CH3:13][C:14]([CH3:23])([CH2:19][N+:20]([O-:22])=[O:21])[CH2:15][C:16]1([CH3:17])[O:6][CH2:5][CH2:4][O:3]1

Participants

5

Reactant 2

HCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 41563834,4-Dimethyl-5-nitropentan-2-one

Product 1

HCID 14638051HCID 14638051, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 65367Trimethylsilyl triflateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 1,2-bis(trimethylsilyloxy)ethane (26.5 g, 128 mmol) in dichloromethane (50 mL) was cooled in a dry ice/isopropanol bath, and trimethylsilyl trifluoromethanesulfonate (2.2 g, 1.0 mmol) was added, followed by the dichloromethane solution of 4,4-dimethyl-5-nitropentan-2-one (50 mL, 19.0 g, 119 mmol) from the previous step. After 30 minutes, the cooling bath was removed and the solution was allowed to warm to room temperature. The solution was filtered through a plug of potassium carbonate and concentrated under reduced pressure to provide 2-(2,2-dimethyl-3-nitropropyl)-2-methyl-[1,3]dioxolane (23.5 g) as a dark oil that was used directly in the next step without further purification.

Workup

  1. customthe cooling bath was removed
  2. filtrationThe solution was filtered through a plug of potassium carbonate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc8b8aaf51d44583aafc7dd54d21a15e
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Linked notes

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