N-Fluorobenzenesulfonimide → HCID 22175082, 화합물

HRID 1797020노트

반응식

HRID 1797020 반응식
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[Li]C(C)(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:31])(=O)=O)=CC=1.CCCCCC.CC(C)=O>CCOCC.C1COCC1>[F:31][C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1]

참가 물질

7

반응물 4

HCID 588007N-FluorobenzenesulfonimideHCID 15635484HCID 15635484, 화합물HCID 21880519Acetone hexaneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 22175082HCID 22175082, 화합물수율 56%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 9 (12.39 g, 0.055 mol) in ether (200 mL) cooled to ≦−70° C. under an atmosphere of argon was slowly added t-BuLi (40 mL, 1.5 M pentane solution). During the addition, the reaction temperature was maintained at ≦−68° C. After the addition was complete the mixture was stirred an additional 60 minutes at ≦−70° C., then transferred via cannula to a stirred solution of N-fluorobenzenesulfonimide (18.92 g) in dry THF (200 mL) which was also cooled to ≦−70° C. under argon. After the addition was complete, the cooling bath was removed and the reaction mixture was allowed to warm up to room temperature. Water (100 mL) was added and the organic phase was separated, dried (MgSO4) and concentrated to give a brown oil. Chromatography (silica gel, hexane-acetone, 9:1) gave the desired product 10 as an orange oil (7.5 g) which contained about 15% starting material. This crude mixture was used directly in the next reaction.

후처리

  1. additionDuring the addition
  2. temperaturethe reaction temperature was maintained at ≦−68° C
  3. additionAfter the addition
  4. temperaturewas also cooled to ≦−70° C. under argon
  5. additionAfter the addition
  6. customthe cooling bath was removed
  7. additionWater (100 mL) was added
  8. customthe organic phase was separated
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a brown oil

출처 및 근거

ORD 기록
ord-0602a33a4fa746b5b5ffb74b78f7b7f3
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034035B2

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