Acetic Acid → HCID 11815865, compound

HRID 1257752Notes

Reaction equation

HRID 1257752 reaction equation
C(O)(=O)C.C[Si]([N:9]=[N+:10]=[N-:11])(C)C.[C:12]1(=[O:17])[CH2:16][CH2:15][CH:14]=[CH:13]1.C(N(CC)CC)C>ClCCl>[N:9]([CH:14]1[CH2:15][CH2:16][C:12](=[O:17])[CH2:13]1)=[N+:10]=[N-:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 135882-Cyclopenten-1-oneHCID 78378Azidotrimethylsilane

Product 1

HCID 11815865HCID 11815865, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid (20 g, 0.33 mol) in dichloromethane (375 mL) was added trimethylsilyl azide (38 g, 0.33 mol), and the mixture was stirred at room temperature for 20 minutes. Then cyclopent-2-enone (9 g, 0.11 mol) was added to the reaction mixture followed by triethylamine (2.22 g, 0.022 mol), and the mixture was stirred at room temperature for 48 hours. The resulting mixture was quenched with aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with brine three times and purified by column chromatography (Hexanes/ethyl acetate=1:3) to give 7.2 g of 3-Azido-cyclopentanone as a colorless liquid (TLC showed two spots), which was used for next step directly. 1H NMR (400 MHz, CDCl3): δ: 4.31-4.26 (m, 1H), 2.46-2.08 (m, 6H).

Workup

  1. stirringthe mixture was stirred at room temperature for 48 hours
  2. customThe resulting mixture was quenched with aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine three times
  5. custompurified by column chromatography (Hexanes/ethyl acetate=1:3)

Sources & evidence

ORD record
ord-77e5c9e558934355817a9c391f56d23d
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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