(4-(Benzyloxy)phenyl)methanol → 4-Benzyloxybenzylamine

HRID 1950628

反応式

HRID 1950628 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:31]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH2:31])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 70043(4-(Benzyloxy)phenyl)methanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azide

生成物 1

HCID 42928454-Benzyloxybenzylamine収率 81%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-benzyloxybenzyl alcohol (3.1 g) in toluene (40 ml) were sequentially added diphenylphosphoryl azide (4.8 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 g), and the solution was stirred for 25 hours at room temperature. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), to a solution of the resulting 1-azidomethyl-4-benzyloxybenzene (3.0 g) in tetrahydrofuran (40 ml) were sequentially added water (3 ml) and triethylphosphine (2.0 ml), and the solution was stirred for 1 hour and 10 minutes at room temperature. The reaction solution was concentrated in vacuo, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.5 g).

後処理

  1. extractionThe solution was extracted with ethyl acetate
  2. washsequentially washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customObtained
  6. customby purifying the residue by silica gel column chromatography (hexane-ethyl acetate system)
  7. stirringthe solution was stirred for 1 hour and 10 minutes at room temperature
  8. concentrationThe reaction solution was concentrated in vacuo
  9. extractionextracted with ethyl acetate
  10. washsequentially washed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated in vacuo
  13. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

出典と根拠

ORDレコード
ord-48e69354d10f44be8e082ccc009f4604
出典データセット
uspto-grants-2013_03
特許番号
US08399520B2

関連ノート

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