Triphenylphosphine → t-Butyloxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]benzene

HRID 1791846ノート

反応式

HRID 1791846 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]([C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44]O)=[CH:39][CH:38]=1)#[N:36].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:44][CH2:43][C:40]2[CH:41]=[CH:42][C:37]([C:35]#[N:36])=[CH:38][CH:39]=2)[CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamateHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 22033522t-Butyloxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]benzene収率 44.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of t-butyloxycarbonylamino-3-hydroxybenzene (418.5 mg; 2 mmol; from step (i) above), triphenylphosphine (629.5 mg; 2.4 mmol) and 2-(4-cyanophenyl)ethanol (353.2 mg; 2.4 mmol) in THF (50 mL), under an atmosphere of nitrogen, was added diethylazodicarboxylate (518 mg; 3 mmol) and the mixture was stirred for one week. Ice cold water was added and the THF was removed by evaporation. The remaining water phase was extracted three times with EtOAc. The combined organic phase was washed twice with 0.2 M NaOH, once with brine, and then dried (Na2SO4). Evaporation followed by flash chromatography using a stepwise gradient of toluene:EtOAc (100:0, 90:10, 80:20 and 60:40) gave 300 mg (44%) of the sub-title compound.

後処理

  1. additionIce cold water was added
  2. customthe THF was removed by evaporation
  3. extractionThe remaining water phase was extracted three times with EtOAc
  4. washThe combined organic phase was washed twice with 0.2 M NaOH, once with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation

出典と根拠

ORDレコード
ord-48a20edaaea94c4a9632062988784803
出典データセット
uspto-grants-2006_07
特許番号
US07074820B2

反応ノート

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