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

HRID 1027907

반응식

HRID 1027907 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-333643b3f30840b5ad90e20e859667a2
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735411B2

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