2-Bromo-cyclopent-2-enol → 2-Isobutyl-cyclopent-2-enol

HRID 28717

반응식

HRID 28717 반응식
Br[C:2]1[CH:3]([OH:7])[CH2:4][CH2:5][CH:6]=1.[CH2:8]([Mg]Br)[CH:9]([CH3:11])[CH3:10]>C1COCC1.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:8]([C:2]1[CH:3]([OH:7])[CH2:4][CH2:5][CH:6]=1)[CH:9]([CH3:11])[CH3:10]

참가 물질

5

반응물 2

HCID 111374622-Bromo-cyclopent-2-enol2회HCID 178418816HCID 178418816, 화합물

생성물 1

HCID 219862102-Isobutyl-cyclopent-2-enol

시약·촉매·용매 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickel촉매HCID 8028Tetrahydrofuran용매

실험 절차

The alcohol (Intermediate D3, 16 mmol) in THF (30 mL) at 0° C. was treated with isobutyl magnesium bromide (40 mmol). The catalyst, 1,3-bis(diphenylphosphino)propane nickel (II) chloride (0.75 mmol) (NiCl2dppp) was added in one portion and the mixture was heated to reflux for 3 h. (see: Organ et al. J. Org. Chem. 1997, 62, 1523, incorporated herein by reference). The reaction mixture was cooled to rt and quenched with sat. NH4Cl solution. The mixture was filtered and partitioned between brine and diethyl ether. The organic layer was removed and dried over Na2SO4, filtered and concentrated under vacuum. The oil was purified by chromatography on SiO2 with 20% EtOAc:Hx to yield 2-isobutyl-cyclopent-2-enol (Intermediate D4). Use of 2-isobutyl-cyclopent-2-enol (Intermediate D4) in Method A produced 4-(2-isobutyl-cyclopent-2-enylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 20).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h. (
  3. customquenched with sat. NH4Cl solution
  4. filtrationThe mixture was filtered
  5. custompartitioned between brine and diethyl ether
  6. customThe organic layer was removed
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe oil was purified by chromatography on SiO2 with 20% EtOAc

출처 및 근거

ORD 기록
ord-6a6ff2f7dfb94c5b87db587bf52ef7fa
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419994B2

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