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Triphenylphosphine → 6-((S)-2-Imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one

HRID 496428
ノート
印刷プレビュー

反応式

HRID 496428 の反応式
[OH:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[N:16]1([CH2:21][C@@H:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)O)[CH:20]=[CH:19][N:18]=[CH:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:16]1([CH2:21][C@H:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[O:1][C:2]2[C:3]([N+:13]([O-:15])=[O:14])=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:20]=[CH:19][N:18]=[CH:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 123928306-Hydroxy-5-nitro-3,4-dihydronaphthalen-1(2H)-oneHCID 60029868(R)-2-imidazol-1-yl-1-pyridin-3-yl-ethanol

生成物 1

HCID 697370746-((S)-2-Imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-nitro-3,4-dihydro-2H-naphthalen-1-one収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-hydroxy-5-nitro-1-tetralone (0.957 g, 4.62 mmol) in dry THF (20 mL) was added (R)-2-imidazol-1-yl-1-pyridin-3-yl-ethanol (0.875 g, 4.62 mmol) followed by triphenylphospine (1.33 g, 5.08 mmol). After approximately 10 min, diethylazodicarboxylate (0.80 mL, 5.08 mmol) was added slowly. The reaction became homogenous. The reaction was allowed to stir at RT overnight. The reaction mixture was concentrated under reduced pressure and the residue was triturated with Et2O to remove some of the phospine by-products. The residue was dissolved in EtOAc and washed with H2O, saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated to give a foam/oil. Purification by chromatography (SiO2, 4-10% MeOH/CH2Cl2) afforded the title compound as a tan foam (1.66 g, 4.39 mmol, 95%). The structure was confirmed by NMR and mass spectrometry. MS m/z 379 (M++H).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with Et2O
  3. customto remove some of the phospine by-products
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O, saturated aqueous NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a foam/oil
  9. customPurification by chromatography (SiO2, 4-10% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-dfe0a61e9e8b4e0f8544aa4efaa5eec3
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06943183B2

反応ノート

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