Triphenylphosphine → HCID 58072009, 화합물

HRID 715680노트

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HRID 715680 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1.O>[O:33]1[CH2:38][CH2:37][CH:36]([O:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:11])([F:12])[F:13])[CH2:35][CH2:34]1

참가 물질

7

반응물 4

HCID 11776Triphenylphosphine2회HCID 74956Tetrahydro-4H-pyran-4-ol2회HCID 27831594-Hydroxy-3-(trifluoromethyl)benzonitrileHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate2회

생성물 1

HCID 58072009HCID 58072009, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

2 g 4-Hydroxy-3-trifluoromethyl-benzonitrile, 5.6 g triphenylphosphine and 1.2 g tetrahydro-4H-pyran-4-ol was suspended in 15 mL tetrahydrofuran at 0° C. before 4.92 g di-tert-butylazodicarboxylate (DBAD) as a solution in 5 mL tetrahydrofuran was added over 15 min. The reaction was warmed to ambient temperature. Additional 2.8 g triphenylphosphine, 0.55 g (5.3 mmol) tetrahydro-4H-pyran-4-ol and 2.46 g di-tert-butylazodicarboxylate (DBAD) in tetrahydrofuran were added and the reaction was stirred overnight. After this time, the reaction was diluted with water and extracted with ethyl acetate (×2). The organic phase was separated and then it was washed with 2N sodium hydroxide, water and saturated sodium chloride, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel chromatography (SiO2: heptane/ethyl acetate) to provide the title compound.

후처리

  1. additionwas added over 15 min
  2. extractionextracted with ethyl acetate (×2)
  3. customThe organic phase was separated
  4. washit was washed with 2N sodium hydroxide, water and saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified with silica gel chromatography (SiO2: heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-59d82300d8bb4e21a896daf231d8eb69
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187478B2

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