Potassium Carbonate → tert-Butyl (2-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)oxy)ethyl)carbamate

HRID 1771944

反応式

HRID 1771944 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([F:16])([F:15])[F:14])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[O:12]=[C:8]1[CH:7]=[C:6]([C:13]([F:16])([F:14])[F:15])[C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:3][CH:4]=2)[O:9]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 53756677-Hydroxy-4-trifluoromethylcoumarin

生成物 1

HCID 86699721tert-Butyl (2-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)oxy)ethyl)carbamate収率 87%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

To a solution of 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one (213 mg, 0.925 mmol) in DMF (1.5 mL) was added tert-butyl (2-bromoethyl)carbamate (416 mg, 1.851 mmol) and K2CO3 (384 mg, 2.776 mmol) at r.t. After stirred at 85° C. for 12 hours, the reaction mixture treated with 10.0 mL of saturated aqueous NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with Ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 9:1 v/v Hexane:Ethyl acetate as solvent to afford title compound (300 mg, 87% yield) as a white solid. 1H NMR 300 MHz (CDCl3) δ 7.64 (d, J=6.0 Hz, 1H), 6.91 (m, 2H), 6.61 (s, 1H), 4.95 (s, 1H), 4.11 (m, 2H), 3.58 (m, 2H), 1.56 (s, 9H), HRMS (m/z): [M+H]+ calculated for C17H18F3NO5. found, 374.1207.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with Ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography

出典と根拠

ORDレコード
ord-461862c62f3b4aeeb3539bc59581e950
出典データセット
uspto-grants-2016_02
特許番号
US09249128B2

関連ノート

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