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1-Cyclohexenyl trifluoromethanesulfonate → 3-(Cyclohex-1-en-1-yl)thiophene

HRID 70741
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HRID 70741 반응식
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.O([C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1)S(C(F)(F)F)(=O)=O>CCOCC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:1]1[CH:5]=[CH:4][C:3]([C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)=[CH:2]1
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참가 물질

6

반응물 2

HCID 3194401-Cyclohexenyl trifluoromethanesulfonateHCID 581760Thiophene-3-boronic acid

생성물 1

HCID 126474723-(Cyclohex-1-en-1-yl)thiophene수율 91.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매
HCID 10340
Sodium Carbonate
용매

실험 절차

3-Thiophene boronic acid (128 mg, 1.00 mmol), cyclohexenyl triflate (230.2 mg, 1.00 mmol) was dissolved in Et2O (4 mL) and 2M Na2CO3 (1 mL). The mixture was degassed and Pd(PPh3)4 (0.05 mmol) added. After stirring at room temperature for 4 h the mixture was filtered through celite, rinsed with Et2O, dried (Na2SO4) and subjected to column chromatography (silica, pentane) to yield 150 mg of a volatile liquid. GC-MS: M+=164.

후처리

  1. customThe mixture was degassed
  2. filtrationwas filtered through celite
  3. washrinsed with Et2O
  4. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-a705f71dfea34badb6cc493f161878ee
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822548B2

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