Potassium tert-butoxide → HCID 178437588, 화합물

HRID 928143노트

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HRID 928143 반응식
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[S:12][C:11]([C:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)=O)=[N:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C.[Cl-].[NH4+]>[Br:7][C:8]1[S:12][C:11]([C:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH2:1])=[N:10][CH:9]=1

참가 물질

6

반응물 2

HCID 23665647Potassium tert-butoxideHCID 178472369HCID 178472369, 화합물

생성물 1

HCID 178437588HCID 178437588, 화합물

시약·촉매·용매 3

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 3283Diethyl Ether용매2회HCID 25517Ammonium Chloride용매

실험 절차

Methyl(triphenyl)phosphonium bromide (774 mg, 2.166 mmol) was suspended in diethyl ether (5 ml) and potassium tert-butoxide (1.78 M in THF, 1.3 ml, 2.314 mmol) was added at 0° C. dropwise, the suspension was stirred 30 min at same temperature. A solution of ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl)carbonyl]cyclohexanecarboxylate (500 mg, 1.444 mmol) in diethyl ether (1 ml) was added dropwise at 0° C. and the mixture was stirred from 0° C. to 5° C. for 1 h 20 min. The mixture was diluted with saturated ammonium chloride and extracted with EtOAc. The organic phase was washed with water, brine, dried with sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (0% to 8% EtOAc in Hexane) to afford ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate as a light yellow oil. MS ESI calc'd. for C14H8BrNO2S [M+H]+ 344, 346. found 344, 346.

후처리

  1. stirringthe mixture was stirred from 0° C. to 5° C. for 1 h 20 min
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0% to 8% EtOAc in Hexane)

출처 및 근거

ORD 기록
ord-8ca826efb640493faa9f22b179d22a6c
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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