Ethanol → Methyl 2-ethoxy-5-nitrobenzoate

HRID 1096582ノート

反応式

HRID 1096582 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:16]=1.CCO.C(OC(N=NC(OC(C)C)=O)=O)(C)C>C1COCC1>[CH2:15]([O:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:16]

参加物

6

反応物 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 87041Methyl 5-nitrosalicylate

生成物 1

HCID 43449037Methyl 2-ethoxy-5-nitrobenzoate収率 90.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 2-hydroxy-5-nitrobenzoate (11.82 g, 60 mmol), triphenylphosphine (17.29 g, 66 mmol) and EtOH (3.03 g, 3.85 ml, 66 mmol) were taken up in THF (150 ml) and cooled in ice. Di-isopropyl-azodicarboxylate (8.31 g, 10 ml, 66 mmol) was added carefully, and the reaction was stirred at RT for 1 hr. The reaction was concentrated in vacuo, and the residue was triturated with EtOAc (50 ml). The solid thus formed was collected by filtration, washed with MTBE and dried in vacuo to give 12.2 g of crude methyl 2-ethoxy-5-nitrobenzoate. The filtrate was evaporated in vacuo, and the resulting residue was triturated with EtOAc (25 ml). The resulting solid was collected by filtration, washed with MTBE and dried in vacuo to give 6.31 g of a second crop of crude methyl 2-ethoxy-5-nitrobenzoate. The combined portions of methyl 2-ethoxy-5-nitrobenzoate were taken up in hot IPA (50 ml) and cooled to RT. The resulting solid was collected by filtration, washed with MTBE and dried in vacuo to give pure methyl 2-ethoxy-5-nitrobenzoate (5.49 g, 40.5%) as a yellow solid.

後処理

  1. temperaturecooled in ice
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe residue was triturated with EtOAc (50 ml)
  4. customThe solid thus formed
  5. filtrationwas collected by filtration
  6. washwashed with MTBE
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-4fcfef290db34923bc252349e44a57a8
出典データセット
uspto-grants-2012_03
特許番号
US08138357B2

反応ノート

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