Triphenylphosphine → HCID 86600007、化合物

HRID 748068ノート

反応式

HRID 748068 の反応式
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:13](O)[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:65]=[N+:66]=[N-:67])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.CCOC(C)=O>[N:65]([CH:13]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=[CH:11][N:10]=1)[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[N+:66]=[N-:67]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68593352HCID 68593352、化合物

生成物 1

HCID 86600007HCID 86600007、化合物収率 30%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 1-(1-benzyl-1H-imidazol-2-yl)-2-ethylbutan-1-ol (1.78 g, 6.88 mmol) in THF (50 mL) at 0° C. was added triphenylphosphine (2.71 g, 10.3 mmol), diethyl azodicarboxylate (1.62 mL, 10.3 mmol) and diphenylphosphorylazide (2.22 mL, 10.3 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with EtOAc and extracted 2 times with 1N HCl. The aqueous layer was washed EtOAc, then basicified with saturated aqueous NaHCO3 and extracted twice with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The resulting oil was purified by column chromatography (SiO2, 100% CHCl3, then MeOH/CHCl3/Et3N, 1:98.5:0.5) to yield a pure oil in 30% yield.

後処理

  1. extractionextracted 2 times with 1N HCl
  2. washThe aqueous layer was washed EtOAc
  3. extractionextracted twice with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was purified by column chromatography (SiO2, 100% CHCl3
  8. customMeOH/CHCl3/Et3N, 1:98.5:0.5) to yield a pure oil in 30% yield

出典と根拠

ORDレコード
ord-bb70cd3cd6134a0b83e469730f9003b3
出典データセット
uspto-grants-2008_07
特許番号
US07399778B2

反応ノート

読み込み中…