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1,2-Dibromopropane → Ethyl 6,7-dihydro-5H-pyrazolo[5,1-B][1,3]oxazine-3-carboxylate

HRID 1697460
ノート
印刷プレビュー

反応式

HRID 1697460 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:11])[NH:8][NH:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20](Br)[CH3:21]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]2[CH2:21][CH2:20][CH2:19][O:11][C:7]=12)=[O:5])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 65531,2-DibromopropaneHCID 11430Potassium CarbonateHCID 238933Ethyl 2,3-dihydro-3-oxo-1H-pyrazole-4-carboxylate

生成物 1

HCID 52228126Ethyl 6,7-dihydro-5H-pyrazolo[5,1-B][1,3]oxazine-3-carboxylate収率 58.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

3-Oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid ethyl ester (13.2 g, 84.5 mmol), potassium carbonate (50 g, 0.3 mol) and N,N-dimethylformamide (500 mL) were combined in a 250 mL round bottom flask, and the mixture was heated to 130° C. 1,2-Dibromo-propane (10.4 mL, 0.10 mol) was added. After 30 minutes, the mixture was partitioned between DCM and water. The aqueous layer was extracted with DCM and the combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The yellow solid was purified by column chromatography (DCM/MeOH) to afford the ester (9.67 g, 58%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ7.62 (s, 1H), 4.41-4.38 (m, 2H), 4.13 (q, 2H), 4.08 (t, 2H, J=6.03 Hz), 2.21-2.15 (m, 2H), 1.21 (t, 3H, J=7.09 Hz).

後処理

  1. customthe mixture was partitioned between DCM and water
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe yellow solid was purified by column chromatography (DCM/MeOH)

出典と根拠

ORDレコード
ord-834678615d694e158ca0aacc84ef59ae
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163901B2

反応ノート

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