Tributylphosphine → HCID 86583975, 화합물

HRID 1270052노트

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HRID 1270052 반응식
[C:1]1([C:7]#[C:8]/[CH:9]=[CH:10]/[CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[CH2:26]([O:28][C:29](=[O:42])[C@@H:30]([O:39][CH2:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[CH3:27].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:42])[C@@H:30]([O:39][CH2:40][CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:12][CH2:11]/[CH:10]=[CH:9]/[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:34][CH:33]=1)[CH3:27]

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 546319840317-08-6HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

생성물 1

HCID 86583975HCID 86583975, 화합물수율 57%

시약·촉매·용매 1

HCID 241Benzene용매

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온도
0 °C

실험 절차

(E)-5-Phenyl-pent-2-en-4-yn-1-ol (328 mg, 2.07 mmol), tributylphosphine (606 mg, 3.0 mmol) and (S)-2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (Tetrahedron Letters, Vol. 35, No. 19, 3139–3142, 1994) (495 mg, 2.07 mmol) were successively dissolved in dry benzene (30 mL) under a nitrogen atmosphere and the solution cooled to 0° C. Solid 1,1′-(azodicarbonyl) dipiperidine (756 mg, 3.0 mmol) was added, the mixture stirred for 10 min., then warmed to room temperature and stirred for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The product was purified by flash column chromatography eluting with toluene graduated to toluene/ethyl acetate (19:1) to give 450 mg (57%) of the title compound.

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe product was purified by flash column chromatography
  6. washeluting with toluene

출처 및 근거

ORD 기록
ord-5f93332082814bc89b8aee7a26890030
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202213B2

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