Ethyl diazoacetate → Ethyl 1,3-dimethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate

HRID 1027907

反応式

HRID 1027907 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:13].F[B-](F)(F)F.C([O+](CC)CC)C.[N+](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N-].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH3:1][C:2]1[C:3]2[CH2:4][CH2:5][CH2:6][CH:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7](=[O:13])[C:8]=2[CH:9]=[C:10]([CH3:12])[CH:11]=1

参加物

7

反応物 4

HCID 12192Ethyl diazoacetateHCID 836193,4-dihydro-5,7-dimethylnaphthalen-1(2H)-oneHCID 516892Sodium BicarbonateHCID 2723982Triethyloxonium tetrafluoroborate

生成物 1

HCID 69225430Ethyl 1,3-dimethyl-5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 5,7-dimethyl-3,4-dihydronaphthalen-1(2H)-one (1 g, 5.74 mmol) in anhydrous CH2Cl2 (20 mL) under nitrogen atmosphere was cooled to 0° C. To this solution was added triethyloxonium tetrafluoroborate (1M in CH2Cl2, 23 mL, 23 mmol), followed with ethyl diazoacetate (1.2 mL, 11.5 mmol). The mixture was stirred at ambient temperature for 16 hrs. The reaction was worked up with saturated sodium bicarbonate, diluted with water and CH2Cl2, and the layers were separated. The organic layer was dried with MgSO4, concentrated and the residue was purified by chromatography on silica gel eluting with 10% EtOAc/Hexanes to provide the title compound. 1H NMR (CD3OD) δ 1.29 (t, 3H), 1.97-2.12 (m, 4H), 2.28-2.30 (m, 3H), 2.30-2.31 (m, 3H), 2.59 (t, 2H), 4.28 (q, 2H), 6.86-6.90 (m, 1H), 6.95-6.99 (m, 1H), 13.17-13.22 (m, 1H). MS (M+H)+ m/z 261.

後処理

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel eluting with 10% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-333643b3f30840b5ad90e20e859667a2
出典データセット
uspto-grants-2014_05
特許番号
US08735411B2

関連ノート

読み込み中…