Triphenylphosphine → HCID 22136507、化合物

HRID 1827486ノート

反応式

HRID 1827486 の反応式
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][C:8]#[C:9][CH2:10]O)([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=[N:18]CCC2)CC1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C([O-])(O)=O.[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-]=[N+]=[N-]>C1COCC1>[Si:5]([O:6][CH2:7][C:8]#[C:9][CH2:10][NH2:18])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])[CH3:12]

参加物

8

反応物 6

HCID 11776TriphenylphosphineHCID 33558AzideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 54618454-((Tert-butyldimethylsilyl)oxy)but-2-yn-1-ol

生成物 1

HCID 22136507HCID 22136507、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice cold, stirred solution of the known 4-(tert-Butyl-dimethyl-silanyloxy)-but-2-yn-1-ol (3.14 g, 15.7 mmol) in THF (50 ml) was added DBU (2.6 ml, 17.4 mmol) and DPPA (3.8 ml, 17.6 mmol). The solution was warmed to room temperature and stirred under an inert atmosphere overnight. The reaction was poured into sat. NaHCO3 and the layers separated. The aqueous layer was re-extracted with EtOAc (2×) and the combined organic layers were dried (Na2SO4), and concentrated under vacuum. Triphenylphosphine (4.61 g, 17.6 mmol) was added to this crude azide dissolved in THF (50 ml), followed by addition of H20 (0.44 ml). The resultant solution was stirred overnight at room temperature, concentrated under reduced pressure and the residue was slurried in a 1:1 mixture of Et2O/pet ether. The solids were removed and the filtrate was concentrated and purified by flash chromatography on silica gel eluting CH2Cl2/MeOH (19:1) to give an amber oil. 1H NMR (CDCl3) δ 4.19 (2H, t, J=1.9 Hz), 3.33 (2H, t, J=1.9 Hz), 0.79 (9H, s), 0.00 (6H, s).

後処理

  1. customthe layers separated
  2. extractionThe aqueous layer was re-extracted with EtOAc (2×)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. additionfollowed by addition of H20 (0.44 ml)
  6. concentrationconcentrated under reduced pressure
  7. additionthe residue was slurried in a 1:1 mixture of Et2O/pet ether
  8. customThe solids were removed
  9. concentrationthe filtrate was concentrated
  10. custompurified by flash chromatography on silica gel
  11. washeluting CH2Cl2/MeOH (19:1)
  12. customto give an amber oil

出典と根拠

ORDレコード
ord-80594267981c498489dc24e21489af5b
出典データセット
uspto-grants-2006_05
特許番号
US07053107B2

反応ノート

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