Water → 2-(4-Oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione

HRID 1384869

반응식

HRID 1384869 반응식
[C:1]1(=[O:14])[N:5]([CH2:6][CH:7]=[O:8])[C:4](=[O:9])[C:3]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:2]12.CO/[CH:17]=[CH:18]/[C:19]([O:21][Si](C)(C)C)=[CH2:20].ClCCl.O>C1C=CC=CC=1.CCOCC.Cl[Zn]Cl>[O:21]=[C:19]1[CH:18]=[CH:17][O:8][CH:7]([CH2:6][N:5]2[C:4](=[O:9])[C:3]3[C:2](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:1]2=[O:14])[CH2:20]1

참가 물질

7

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 76201Phthalylglycine aldehydeHCID 5366448trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene

생성물 1

HCID 219366682-(4-Oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione수율 69%

시약·촉매·용매 2

HCID 11106649Ethyl ether, compd. with zinc chloride (3:1)촉매HCID 241Benzene용매

실험 절차

To a mixture of phthalimidoacetaldehyde (64 g, 0.34 mol) and trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (81.5 g, 0.38 mol) in benzene (600 ml) stirred for 15 min. under nitrogen was added dropwise a 45% solution of zinc chloride diethyl ether complex in dichloromethane (55.5 ml, 0.17 mol) at 0° C. The reaction was allowed warm up to room temperature overnight. To the reaction mixture was added water (500 ml) and the resulting mixture was extracted with ethyl acetate (200 ml). The organic extract was washed successively with 1.0 N hydrochloric acid (2×200 ml) and brine (200 ml). The organic phase was dried (Na2SO4), filtered and the solvent evaporated in vacuo which afforded a slowly crystallising oil (98 g). To the solid was added a mixture of ethyl acetate and diethyl ether (400 ml, 1:1) and the resulting precipitate was filtered off, washed with a small portion of diethyl ether and dried at 50° C. for 1h affording 59.8 g (69%) of 2-(4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid. The filtrate was evaporated in vacuo and the residue purified by column chromatography on silica gel (1 L) using a mixture of ethyl acetate and heptane (1:2) as eluent. Pure fractions were collected and the solvent evaporated in vacuo to almost dryness, the solid was filtered off and dried in vacuo at 50° C. for 16 h affording an additional 15 g (17%) of 2-(4-oxo-3,4-dihydro-2H-pyran-2-ylmethyl)-isoindole-1,3-dione as a solid.

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate (200 ml)
  2. extractionThe organic extract
  3. washwas washed successively with 1.0 N hydrochloric acid (2×200 ml) and brine (200 ml)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo which
  7. customafforded
  8. customa slowly crystallising oil (98 g)
  9. additionTo the solid was added
  10. additiona mixture of ethyl acetate and diethyl ether (400 ml, 1:1)
  11. filtrationthe resulting precipitate was filtered off
  12. washwashed with a small portion of diethyl ether
  13. dry with materialdried at 50° C. for 1h

출처 및 근거

ORD 기록
ord-a1a6bbbffd684c2b91fffa9964526d00
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262044B1

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