홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Sodium hydride → (3Z)-3-(4,4-dimethyl-2-oxopentylidene)spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropan]-2-one

HRID 1888880
노트
인쇄 미리보기

반응식

HRID 1888880 반응식
COP([CH2:7][C:8](=[O:14])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=O)OC.[H-].[Na+].[C:17]12([CH:23]3[CH2:24][CH2:25][CH:20]1[C:21](=[O:27])[C:22]3=O)[CH2:19][CH2:18]2>C1COCC1>[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8](=[O:14])/[CH:7]=[C:22]1/[C:21](=[O:27])[CH:20]2[C:17]3([CH2:18][CH2:19]3)[CH:23]/1[CH2:24][CH2:25]2.[CH3:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8](=[O:14])/[CH:7]=[C:22]1\[C:21](=[O:27])[CH:20]2[C:17]3([CH2:18][CH2:19]3)[CH:23]\1[CH2:24][CH2:25]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 144441Spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropane]-2,3-dioneHCID 25112585(4,4-Dimethyl-2-oxo-pentyl)-phosphonic acid dimethyl ester

생성물 2

HCID 68537264(3Z)-3-(4,4-dimethyl-2-oxopentylidene)spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropan]-2-oneHCID 68541247(3E)-3-(4,4-dimethyl-2-oxopentylidene)spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropan]-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A solution (4,4-dimethyl-2-oxo-pentyl)-phosphonic acid dimethyl ester (1.249 g) in THF (40 ml) was cooled to 0° C. under an argon atmosphere and sodium hydride (0.268 g) was added in 4 portions. Spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropane]-2,3-dione (1.023 g) dissolved in THF (30 ml) was then added dropwise to the reaction mixture. The mixture was then stirred for further 15 minutes at 0° C. (until completion of reaction according to TLC analysis). The reaction mixture was partitioned between water/3N HCl and AcOEt, the layers were separated, the organic layer washed with saturated, aqueous NaCl, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography with heptane/AcOEt: 100% to 95% as eluant to give (3E)-3-(4,4-dimethyl-2-oxopentylidene)spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropan]-2-one (0.284 g) and (3Z)-3-(4,4-dimethyl-2-oxopentylidene)spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropan]-2-one (0.287 g) as yellow oils, respectively, that were directly used in the next step. Assignment of the E/Z isomers was done by NMR.

후처리

  1. additionwas then added dropwise to the reaction mixture
  2. custom(until completion of reaction according to TLC analysis)
  3. customThe reaction mixture was partitioned between water/3N HCl and AcOEt
  4. customthe layers were separated
  5. washthe organic layer washed with saturated, aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography with heptane/AcOEt

출처 및 근거

ORD 기록
ord-911be6a1b2504d639609e89e6c5f6592
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08501940B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트