Iodine → HCID 66749494、化合物

HRID 537037ノート

反応式

HRID 537037 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][CH:11]=[N:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[I:27]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][C:11]([I:27])=[N:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14]

参加物

6

反応物 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 2733832Lithium HexamethyldisilazideHCID 13290634Methyl 5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate

生成物 1

HCID 66749494HCID 66749494、化合物収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a round bottom flask were added methyl 5-(2-chlorophenyl)-1,3-oxazole-4-carboxylate (2.25 g, 9.5 mmol) and THF (50 mL). The mixture was cooled to −78° C. LiHMDS (1M in hexane, 12.3 mL, 12.3 mmol) was added dropwise. The mixture was allowed to stir at −78° C. for 1 h. Iodine (3.60 g, 14.2 mmol) was added and the mixture was allowed to stir at −78° C. for 20 min. The mixture was allowed to warm to rt and stir overnight. The reaction mixture was poured into 10% sodium thiosulfate (100 mL) and was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered, and concentrated to give methyl 5-(2-chlorophenyl)-2-iodo-1,3-oxazole-4-carboxylate (3.0 g, 87%) which was used without further purification.

後処理

  1. stirringto stir at −78° C. for 20 min
  2. temperatureto warm to rt
  3. stirringstir overnight
  4. extractionwas extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-49dbbc1bcc7942c9a3ceadd328f611a5
出典データセット
uspto-grants-2014_10
特許番号
US08859768B2

反応ノート

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