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

HRID 520351

반응식

HRID 520351 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 10057735HCID 10057735, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c51c2f503c1544b8b3d69fba829277c1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326973B2

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