Diethyl Oxalate → HCID 178473089, 화합물

HRID 389925노트

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HRID 389925 반응식
[Na].[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([Cl:24])=[CH:12][C:11]=1[C:25](=[O:27])[CH3:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:28]([O:30][C:31](=[O:37])[C:32](OCC)=[O:33])[CH3:29]>C(O)(=O)C>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([Cl:24])=[CH:12][C:11]=1[C:25](=[O:27])[CH:26]=[C:32]([OH:33])[C:31]([O:30][CH2:28][CH3:29])=[O:37])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 7268Diethyl OxalateHCID 5360545SodiumHCID 179636911-(2,4-Bis(benzyloxy)-5-chlorophenyl)ethanone

생성물 1

HCID 178473089HCID 178473089, 화합물수율 98%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Sodium metal (1.35 g, 58 mmol) was cut into small pieces, rinsed with hexane to remove mineral oil, and added portion wise to anhydrous EtOH (100 ml) under a nitrogen atmosphere over a period of 20 min. The reaction mixture was stirred for a further 10 min until all sodium had reacted. 1-[2,4-bis(benzyloxy)-5-chlorophenyl]ethanone (10 g, 27.3 mmol) was added portion wise over 5 min, and the resulting suspension was then stirred for further 5 min at RT. Diethyloxalate (6 ml, 43 mmol) was added, resulting in a thick yellow coloured precipitate. The reaction mixture was heated to reflux for 4 h, affording a dark homogeneous solution, which, upon cooling, produced a solid mass to which acetic acid (6 ml) was added. The mixture was triturated to afford a yellow solid, which was filtered, washed sequentially with water, EtOH, and Et2O, and then dried under vacuo to afford the title compound ethyl 4-(2,4-bis(benzyloxy)-5-chlorophenyl)-2-hydroxy-4-oxobut-2-enoate (12.4 g, 98%) as a yellow solid.

후처리

  1. washrinsed with hexane
  2. customto remove mineral oil
  3. additionadded portion wise to anhydrous EtOH (100 ml) under a nitrogen atmosphere over a period of 20 min
  4. customhad reacted
  5. stirringthe resulting suspension was then stirred for further 5 min at RT
  6. customresulting in a thick yellow coloured precipitate
  7. temperatureThe reaction mixture was heated
  8. temperatureto reflux for 4 h
  9. customaffording a dark homogeneous solution, which
  10. temperatureupon cooling
  11. additionwas added
  12. customThe mixture was triturated
  13. customto afford a yellow solid, which
  14. filtrationwas filtered
  15. washwashed sequentially with water, EtOH, and Et2O
  16. customdried under vacuo

출처 및 근거

ORD 기록
ord-382bff0d3b7643f99893502da182d0ad
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383616B2

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