Dimethylformamide → HCID 57738866、化合物

HRID 1715735ノート

反応式

HRID 1715735 の反応式
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([OH:16])[C:8]([OH:17])=[C:7]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:2].Br[CH2:25][CH2:26][CH2:27]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]2[O:17][CH2:25][CH2:26][CH2:27][O:16][C:9]2=[C:10]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:2]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 57738870HCID 57738870、化合物

生成物 1

HCID 57738866HCID 57738866、化合物収率 83.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
105 °C

実験手順

To a 500-mL round-bottom flask containing a stir bar and an argon atmosphere was added diethyl 1-(2-ethoxy-2-oxoethyl)-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate (48.00 g, 146 mmol), 1,3-dibromopropane (29.48 g, 146 mmol), anhydrous potassium carbonate (50.36 g, 364 mmol), and anhydrous dimethylformamide (DMF) (250 mL). The reaction was heated to 105° C. and became lime green after about 30 minutes. The reaction was stirred for 12 hours, during which, it became yellow, and was cooled to room temperature. The mixture was poured into DI water (500 mL), the solids were collected via vacuum filtration, and washed with several portions of DI water. The solids were recrystallized from hot methanol to yield 44.90 g (80%) of a yellow solid. mp 139.7-139.9° C.; 1H NMR (300 MHz, CDCl3): δ 5.43 (s, 2H), 4.30 (q, 4H, J=7.7 Hz), 4.22 (q, 2H, J=8.0 Hz), 4.20 (t, 6H, J=63 Hz), 2.25 (p, 2H, J=6.3 Hz), 1.34 (t, 6H, J=7.7 Hz), 1.28 (t, 3H, J=8.0 Hz); 13C NMR (75 MHz, CDCl3): δ 169.6, 161.0, 142.7, 114.1, 71.7, 61.5, 60.9, 48.0, 33.4, 14.5, 14.4; HRMS (EI): Calcd for C17H23NO8 ([M]+), 369.1424, found m/z, 369.1417; Anal. Calcd for C17H23NO8: C, 55.28; H3, 6.28; N, 3.79%, found: C, 55.29; H, 6.37; N, 3.80

後処理

  1. additionTo a 500-mL round-bottom flask containing a stir bar
  2. customafter about 30 minutes
  3. temperaturewas cooled to room temperature
  4. filtrationthe solids were collected via vacuum filtration
  5. washwashed with several portions of DI water
  6. customThe solids were recrystallized from hot methanol

出典と根拠

ORDレコード
ord-7e6311a4d3d14124ab579aa0e1981d63
出典データセット
uspto-grants-2010_09
特許番号
US07799932B2

反応ノート

読み込み中…