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Dimethyl Sulfoxide → 2-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal

HRID 1847003
ノート
印刷プレビュー

反応式

HRID 1847003 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]([O:28][CH2:29][O:30][CH3:31])[CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][C:16]1=[O:27].C(N(CC)CC)C>ClCCl>[CH3:31][O:30][CH2:29][O:28][CH:13]([CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][C:16]1=[O:27])[CH:12]=[O:11]
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

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 867249321-[3-Hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one

生成物 1

HCID 867249342-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
4 回

反応条件

温度
-78 °C

実験手順

Oxalyl chloride (0.032 ml, 0.374 mmol) was dissolved in dichloromethane (2 ml). A solution of dimethyl sulfoxide (0.053 ml, 0.748 mmol) in dichloromethane (0.5 ml) was added to this solution at −78° C. and the mixture was stirred for 30 minutes. While maintaining the temperature at −78° C., a solution of 1-[3-hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one (100 mg, 0.340 mmol) in dichloromethane (3 ml) was further added and the mixture was stirred for 40 minutes. While maintaining the temperature at −78° C., triethylamine (0.261 ml, 1.870 mmol) was added and the mixture was stirred for 30 minutes. The temperature was raised to 0° C., the reaction solution was stirred for 2 hours, then diluted with dichloromethane and washed with water. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to yield 109 mg (quantitative) of the title compound in the form of an orange oily product. The product was used as such for the next step without purification.

後処理

  1. stirringthe mixture was stirred for 40 minutes
  2. temperatureWhile maintaining the temperature at −78° C.
  3. stirringthe mixture was stirred for 30 minutes
  4. temperatureThe temperature was raised to 0° C.
  5. stirringthe reaction solution was stirred for 2 hours
  6. washwashed with water
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-56999e63d5554c5b89b6ba4b68c02fff
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952010B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート