Nitric Acid → 7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

HRID 2292483ノート

反応式

HRID 2292483 の反応式
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].CCCCCC>C(O)(=O)C>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 8058HexaneHCID 11805831HCID 11805831、化合物

生成物 1

HCID 107531427-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
24 °C

実験手順

A solution of 7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan (10.0 g, 49.0 mmol) in glacial acetic acid 80 mL) is treated with 70% nitric acid (4.0 mL, 63.7 mmol) dropwise, and allowed to stir at 24° C. for 4 h. TLC (hexane) is used to monitor reaction progress. The reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL). The Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL), dried (MgSO4), filtered and evaporated to a red solid (9.12 g). Crystallization from hexane provides 7-tert-butyl-3,3-dimethyl-5-nitro-2,3-dihydrobenzo[b]furan as an orange solid.

後処理

  1. customreaction progress
  2. customThe reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL)
  3. washThe Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a red solid (9.12 g)
  7. customCrystallization from hexane

出典と根拠

ORDレコード
ord-f6ad421a5c99424eb18fbb7e820671a8
出典データセット
uspto-grants-1997_11
特許番号
US05684002

反応ノート

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