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

Triethylamine → HCID 91368801, 화합물

HRID 551662
노트
인쇄 미리보기

반응식

HRID 551662 반응식
[CH2:1]([CH:4]([CH2:10][CH:11]=[CH2:12])[CH:5]=[CH:6][C:7](O)=O)[CH:2]=[CH2:3].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[H-].[Na+].COP([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])(OC)=O>C1C=CC=CC=1.C(OCC)(=O)C.O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([C:4]1[CH2:10][C@@H:11]2[C@H:6]([CH:5]=1)[C:7](=[CH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:12]2)[CH:2]=[CH2:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 85940291HCID 85940291, 화합물

생성물 1

HCID 91368801HCID 91368801, 화합물

시약·촉매·용매 4

HCID 241
Benzene
용매
HCID 1140Toluene용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

4-Allylhepta-2,6-dienoic acid (2.00 g, 12.0 mmol) was dissolved in benzene (5 mL). To the solution, oxalyl chloride (7.01 g, 55.2 mmol) was added under ice cooling, and the mixture was stirred in this state for 1 hour. The mixture was further stirred at room temperature for 30 minutes, then heated to 80° C., and stirred for 1 hour. Then, the solvent was distilled off under reduced pressure. To the residue, toluene was added, and the solvent was distilled off again under reduced pressure. The residue was dissolved in toluene (20 mL). This solution was added dropwise to a toluene solution (30 mL) of triethylamine (4.41 g, 43.68 mmol) heated in advance to reflux, and the mixture was further stirred for 2.5 hours. The reaction solution was allowed to cool, then diluted with saturated saline and ethyl acetate, and filtered through Xelite. The filtrate was separated into aqueous and organic layers. Then, the organic layer was washed with 1 N hydrochloric acid and saturated saline in this order, then dried over anhydrous magnesium sulfate, and then filtered. This filtrate was added to a reaction solution prepared in advance by adding sodium hydride (>65% oil, 457.1 mg, 12 mmol) to a tetrahydrofuran solution (20 mL) of tert-butyl dimethoxyphosphorylacetate (3.03 g, 12 mmol) under ice cooling, and the mixture was stirred for 1 hour. The solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil substance (0.63 g, 16%, E/Z mixture).

후처리

  1. stirringThe mixture was further stirred at room temperature for 30 minutes
  2. stirringstirred for 1 hour
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. additionTo the residue, toluene was added
  5. distillationthe solvent was distilled off again under reduced pressure
  6. dissolutionThe residue was dissolved in toluene (20 mL)
  7. temperatureheated in advance
  8. temperatureto reflux
  9. stirringthe mixture was further stirred for 2.5 hours
  10. temperatureto cool
  11. filtrationfiltered through Xelite
  12. customThe filtrate was separated into aqueous and organic layers
  13. washThen, the organic layer was washed with 1 N hydrochloric acid and saturated saline in this order
  14. dry with materialdried over anhydrous magnesium sulfate
  15. filtrationfiltered
  16. additionThis filtrate was added to a reaction solution
  17. customprepared in advance
  18. stirringthe mixture was stirred for 1 hour
  19. distillationThe solvent was distilled off under reduced pressure
  20. customto obtain the compound of interest as a pale yellow oil substance (0.63 g, 16%, E/Z mixture)

출처 및 근거

ORD 기록
ord-0887c56c37c14b15a07a9b91b276e893
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947738B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트