Triethylamine → HCID 18756251、化合物

HRID 434060ノート

反応式

HRID 434060 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[N+:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#[C-:19].CCN(CC)CC>CN(C=O)C.C1COCC1.C(Cl)Cl>[CH3:24][O:23][C:21]([C:20]1[N:18]=[CH:19][O:6][C:4]=1[C:3]1[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])=[O:22]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 679472-Chloro-6-fluorobenzoic acidHCID 547815Methyl isocyanoacetate

生成物 1

HCID 18756251HCID 18756251、化合物収率 24%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-chloro-6-fluorobenzoic acid (2.14 g, 12.3 mmol), CH2Cl2 (50 ml), and DMF (2 drops) at room temperature under N2 was added oxalyl chloride (9.2 ml, 18.4 mmol) dropwise. The mixture was stirred for 3 h and the volatiles were removed under reduced pressure to give the crude acid chloride. The crude acid chloride and methyl isocyanoacetate (1.23 g, 12.3 mmol) were dissolved in THF (20 ml) at room temperature under N2 and Et3N (6.8 ml, 49.2 mmol) was added dropwise over a period of 30 minutes. The reaction was allowed to stir for 22 h followed by dilution with Et2O, extraction with H2O, 1N HCl, H2O, brine, dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/Et2O gradient) gave 4-methoxycarbonyl-5-(2-chloro-6-fluorophenyl)oxazole (0.74 g, 24%).

後処理

  1. customthe volatiles were removed under reduced pressure
  2. customto give the crude acid chloride
  3. stirringto stir for 22 h
  4. extractionfollowed by dilution with Et2O, extraction with H2O, 1N HCl, H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-e7c26230571848e4a0c799777005a8f7
出典データセット
uspto-grants-2003_12
特許番号
US06670373B1

反応ノート

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