Tributylphosphine → HCID 86583975、化合物

HRID 1270052ノート

反応式

HRID 1270052 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 86583975HCID 86583975、化合物収率 57%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
0 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-5f93332082814bc89b8aee7a26890030
出典データセット
uspto-grants-2007_04
特許番号
US07202213B2

反応ノート

読み込み中…