Methyl iodide → ethyl 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 253116

反応式

HRID 253116 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].[O:7]1[CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][NH:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.IC>CC(C)=O.ClCCl>[CH3:1][N:10]1[CH2:11][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:7][C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]1=2

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

生成物 1

HCID 10608998ethyl 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate収率 65.5%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

In a sealable vessel, potassium carbonate (56 mg, 0.41 mmol) was added to a solution of (±)-ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (60 mg, 0.29 mmol) and iodomethane (22 □L, 0.35 mmol) in acetone (2 mL). The vessel was sealed and the reaction mixture was stirred at 60° C. for 24 h. The mixture was cooled to ambient temperature, diluted with dichloromethane (60 mL), and the organic layer was extracted with water (10 mL) and half-saturated brine (10 mL). The organic layer was dried over sodium sulfate and concentrated. Purification of the concentrate by flash column chromatography (5% to 10% EtOAc/hexane) afforded the title compound (43 mg, 0.19 mmol). MS m/z: 222 (M+1).

後処理

  1. customThe vessel was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionthe organic layer was extracted with water (10 mL) and half-saturated brine (10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the
  7. concentrationconcentrate by flash column chromatography (5% to 10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-ce2e6b8bdf6e4afc9cc84d2f7229f786
出典データセット
uspto-grants-2011_01
特許番号
US07872009B2

関連ノート

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