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

HRID 496407ノート

反応式

HRID 496407 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:29]=[CH:28][CH:27]=[CH:26][CH:25]=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.CO.C(Cl)Cl>[N+:13]([C:3]1[C:2]([O:1][C@@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:12])([O-:15])=[O:14]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 707108(R)-2-Imidazol-1-yl-1-phenyl-ethanolHCID 5462977Diethyl azodicarboxylateHCID 123928306-Hydroxy-5-nitro-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 600298755-nitro-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one収率 80.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a solution of 6-hydroxy-5-nitro-1-tetralone (2.09 g, 10.1 mmol) in dry THF (50 mL) was added (R)-2-imidazol-1-yl-1-phenyl-ethanol (2.28 g, 12.1 mmol) followed by triphenylphosphine (3.18 g, 12.1 mmol). After approximately 10 min, diethylazodicarboxylate (1.9 mL, 12.1 mmol) was added slowly. The reaction became homogenous within 2 min. 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 MgSO4, and concentrated to give a foam/oil. Purification by chromatography (SiO2, 10 to 20% acetone/Cl2Cl2 then 5% MeOH/CH2Cl2) afforded the title compound as a light brown foam (3.06 g, 8.1 mmol, 80%). The structure was confirmed by NMR and mass spectrometry. MS m/z 378 (M++H).

後処理

  1. waitThe reaction became homogenous within 2 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was triturated with Et2O
  4. customto remove some of the phospine by-products
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with H2O, saturated aqueous NaHCO3 and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customto give a foam/oil
  10. customPurification by chromatography (SiO2, 10 to 20% acetone/Cl2Cl2

出典と根拠

ORDレコード
ord-24f9a1b636ea4b21b0ed361ea093fddf
出典データセット
uspto-grants-2005_09
特許番号
US06943183B2

反応ノート

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