Trimethylsilyldiazomethane → Methyl 2-amino-4,6-dimethoxybenzoate

HRID 871392ノート

反応式

HRID 871392 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][Si](C=[N+]=[N-])(C)C>CO.C1COCC1.C(OCC)C>[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([O:6][CH3:15])=[O:5]

参加物

6

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 116584562-Amino-4,6-dimethoxybenzoic acid

生成物 1

HCID 11550253Methyl 2-amino-4,6-dimethoxybenzoate収率 76%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 2-amino-4,6-dimethoxybenzoic acid (7.888 g, 40 mmol) in MeOH (40 mL) and THF (40 mL) at room temperature was dropped 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether. The mixture was stirred at room temperature overnight. After the solvent was evaporated under reduced pressure, water and EtOAc was added to the residue. The organic layer was separated, dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with 20-40% EtOAc/hexane as eluants to afford methyl 2-amino-4,6-dimethoxybenzoate as a solid (6.462 g, 76%). 1H NMR (300 MHz, CDCl3) δ 5.83 (d, 1H), 5.78 (d, 1H), 5.53 (br, 2H), 3.86 (s, 3H), 3.80 (s, 3H), 3.77 (s, 3H); LC-MS (ESI) m/z 212 (M+H)+.

後処理

  1. customAfter the solvent was evaporated under reduced pressure, water and EtOAc
  2. additionwas added to the residue
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography with 20-40% EtOAc/hexane as eluants

出典と根拠

ORDレコード
ord-db9d0c1db7724b09ab51498698d30c21
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

反応ノート

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