Triphenylphosphine → HCID 59599582、化合物

HRID 2267056ノート

反応式

HRID 2267056 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 59599582HCID 59599582、化合物収率 50.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bcd7229c1bcf42b98d08a445d65c2a01
出典データセット
uspto-grants-2010_12
特許番号
US07858646B2

反応ノート

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