1-Butanaminium, N,N,N-tributyl-, azide → HCID 10057735, compound

HRID 520351

Reaction equation

HRID 520351 reaction equation
FC(F)(F)S(O[C@@H:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:8]1=[O:14])(=O)=O.[N-:17]=[N+:18]=[N-:19].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.CCOC(C)=O>[N:17]([C@H:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:8]1=[O:14])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 10106752HCID 10106752, compound

Product 1

HCID 10057735HCID 10057735, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl trifluoromethanesulfonate (10 g) in DCM (10 mL) was added tetra-n-butylammonium azide (11.1 g). The reaction mixture was stirred at rt for 16 hr. The reaction was diluted with EtOAc, washed with water, sat. NaHCO3, citric acid, water, and sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield an oil. The crude product was purified by silica gel chromatography (0-100% EtOAc in hexane) to yield (S)-3-azido-4,4-dimethyldihydrofuran-2(3H)-one as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 3.87-4.02 (3H, m), 1.17 (3H, s), 1.02 (3H, s).

Workup

  1. washwashed with water, sat. NaHCO3, citric acid, water, and sat. NaCl
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield an oil
  6. customThe crude product was purified by silica gel chromatography (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-c51c2f503c1544b8b3d69fba829277c1
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Linked notes

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