Tetrahydrofuran → 4-Tert-butyl-2-[5-(2-methyl-2-methoxycarbonylpropyl)benzofuran-2-yl]thiazole

HRID 487690노트

반응식

HRID 487690 반응식
C([N-]C(C)C)(C)C.[Li+].O1CCCC1.[CH3:14][CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17].[C:21]([C:25]1[N:26]=[C:27]([C:30]2[O:31][C:32]3[CH:38]=[CH:37][C:36]([CH2:39]Cl)=[CH:35][C:33]=3[CH:34]=2)[S:28][CH:29]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C)P(=O)(N(C)C)N(C)C.CCCCCC>[C:21]([C:25]1[N:26]=[C:27]([C:30]2[O:31][C:32]3[CH:38]=[CH:37][C:36]([CH2:39][C:15]([CH3:20])([C:16]([O:18][CH3:19])=[O:17])[CH3:14])=[CH:35][C:33]=3[CH:34]=2)[S:28][CH:29]=1)([CH3:24])([CH3:23])[CH3:22]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 11039Methyl isobutyrateHCID 2724682Lithium diisopropylamideHCID 19603727HCID 19603727, 화합물

생성물 1

HCID 190927974-Tert-butyl-2-[5-(2-methyl-2-methoxycarbonylpropyl)benzofuran-2-yl]thiazole

시약·촉매·용매 2

HCID 8058Hexane용매HCID 12679Hexamethylphosphoramide용매2회

실험 절차

To a cooled suspension of lithium diisopropylamide {(1.45 mM tetrahydrofuran and n-hexane solution), 3.7 ml} and methyl 2-methylpropionate (0.6 g), a dried hexamethylphosphoric triamide (0.5 ml) was added at -65 to -57° C. Subsequently, 4-tert-butyl-2-(5-chloromethylbenzofuran-2-yl)thiazole was added to the mixture in small portions. After being stirred for 30 minutes at the same temperature, additive hexamethylphosphoric triamide (1.5 ml) was added to the mixture. The reaction mixture was gradually elevated to -10° C. for 1 hour. The resulting mixture was poured into ice-water and extracted with diethyl ether. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate (20:1). The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-[5-(2-methyl-2-methoxycarbonylpropyl)benzofuran-2-yl]thiazole (0.43 g).

후처리

  1. additionwas added to the mixture
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of n-hexane and ethyl acetate (20:1)
  8. additionThe fractions containing object compound
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-26ceb3aedc3c40f89836f1800e4fdb82
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05296495

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