4-Aminophenol → tert-Butyl 3-amino-4-hydroxybenzoate

HRID 25263

反応式

HRID 25263 の反応式
N[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([O:16]C(OC(C)(C)C)=O)=O)([CH3:12])([CH3:11])[CH3:10].C([N:27](C(C)C)CC)(C)C>C1COCC1>[C:14]([C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([NH2:27])[CH:3]=1)([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:16]

参加物

5

反応物 3

HCID 4034-AminophenolHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

生成物 1

HCID 11160103tert-Butyl 3-amino-4-hydroxybenzoate収率 96.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-aminophenol (10.9 g, 100 mmol) in THF (150 mL) cooled in an ice bath was added di-tert-butyl-dicarbonate (21.8 g, 100 mmol) followed by diisopropylethylamine (17.4 mL, 100 mmol). The mixture was stirred at room temperature overnight and concentrated. The residue was taken up in ethyl acetate and the solution was washed with brine, dried (MgSO4), and concentrated. Purification on a silica gel column eluting with 5% methanol/40% ethyl acetate hexane gave 4Boc-aminophenol (20.1 g, 96%). MS(NH3—CI): (M+NH3+H)=227.

後処理

  1. concentrationconcentrated
  2. washthe solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification on a silica gel column
  6. washeluting with 5% methanol/40% ethyl acetate hexane

出典と根拠

ORDレコード
ord-a263a6c6aab24b52ae051db78b79b634
出典データセット
uspto-grants-2005_02
特許番号
US06858626B2

関連ノート

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