Iodine → HCID 66749494, 화합물

HRID 537037노트

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HRID 537037 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 66749494HCID 66749494, 화합물수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49dbbc1bcc7942c9a3ceadd328f611a5
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859768B2

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