Isopropanol → 3-Methoxy-5-(propan-2-yloxy)aniline

HRID 1616945ノート

反応式

HRID 1616945 の反応式
[NH2:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH:11]([OH:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:11]([O:14][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1)[NH2:1])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 119535163-Amino-5-methoxyphenol

生成物 1

HCID 115719053-Methoxy-5-(propan-2-yloxy)aniline収率 58.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-amino-5-methoxyphenol (5.44 g, 39.1 mmol), isopropyl alcohol (3.6 ml, 47 mmol) and triphenylphosphine (12.0 g, 47 mmol) in THF, was added diethyl azodicarboxylate (7.4 ml, 47 mmol). The reaction mixture was stirred for 16 h and the solvent was removed. The residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes to afford the title compound (4.13 g). MS m/z: 182 [M+H]+

後処理

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes

出典と根拠

ORDレコード
ord-689972f5ed864150a37c67ba9247ea6a
出典データセット
uspto-grants-2014_07
特許番号
US08765779B2

反応ノート

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