Triphenylphosphine → HCID 59599582, 화합물

HRID 2267056

반응식

HRID 2267056 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:34][CH2:35][C:36]1[CH:37]=[C:38]([S:42][C:43]2[CH:44]=[N:45][CH:46]=[C:47]([CH:50]=2)[C:48]#[N:49])[CH:39]=[CH:40][CH:41]=1.[OH:51][C:52]1[C:57]([CH3:58])=[C:56](O)[CH:55]=[CH:54][C:53]=1[C:60](=[O:62])[CH3:61]>C1COCC1>[C:60]([C:53]1[CH:54]=[CH:55][C:56]([O:34][CH2:35][C:36]2[CH:37]=[C:38]([S:42][C:43]3[CH:44]=[N:45][CH:46]=[C:47]([CH:50]=3)[C:48]#[N:49])[CH:39]=[CH:40][CH:41]=2)=[C:57]([CH3:58])[C:52]=1[OH:51])(=[O:62])[CH3:61]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5921391-(2,4-Dihydroxy-3-methylphenyl)ethan-1-oneHCID 5363146Diisopropyl azodicarboxylateHCID 685380695-(3-(Hydroxymethyl)phenylthio)nicotinonitrile

생성물 1

HCID 59599582HCID 59599582, 화합물수율 50.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add triphenylphosphine (5.24 g, 20.0 mmol) and diisopropylazodicarboxylate (4.04 g, 20.0 mmol) to a solution of 5-(3-(hydroxymethyl)phenylthio)nicotinonitrile (4.84 g, 20.0 mmol) and 1-(2,4-dihydroxy-3-methylphenyl)ethanone (3.32 g, 20.0 mmol) in THF (100 mL). Stir the reaction for 24 h. Quench the reaction with water and extract with EtOAc. Dry, filter and concentrate. Purify the residue by flash chromatography on silica gel eluting with a mixture of EtOAc and hexanes (15:85 to 20:80) to give an off-white solid. Recrystallize the solid from a mixture of EtOAc and hexanes to afford the title compound (3.94 g, 50%): 1H NMR (CDCl3) δ 2.14 (s, 3H), 2.57 (s, 3H), 5.18 (s, 2H), 6.44 (d, J=9.0 Hz, 1H), 7.46-7.49 (m, 3H), 7.52 (s, 1H), 7.59 (d, J=9.0 Hz, 1H), 7.62-7.63 (m, 1H), 8.63-8.64 (m, 2H), 12.78 (s, 1H).

후처리

  1. customthe reaction for 24 h
  2. customQuench
  3. customthe reaction with water
  4. extractionextract with EtOAc
  5. customDry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel eluting
  9. additionwith a mixture of EtOAc and hexanes (15:85 to 20:80)
  10. customto give an off-white solid
  11. customRecrystallize the solid
  12. additionfrom a mixture of EtOAc and hexanes

출처 및 근거

ORD 기록
ord-bcd7229c1bcf42b98d08a445d65c2a01
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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