Tributylphosphine → (Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester

HRID 413932ノート

反応式

HRID 413932 の反応式
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[CH3:32]/[C:33](/[C:37]#[C:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[CH:34]/[CH2:35][OH:36].[CH2:45]([O:47][C@@H:48]([CH2:54][C:55]1[CH:60]=[CH:59][C:58](O)=[CH:57][CH:56]=1)[C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH3:46]>C1C=CC=CC=1>[CH2:52]([O:51][C:49](=[O:50])[C@@H:48]([O:47][CH2:45][CH3:46])[CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:36][CH2:35]/[CH:34]=[C:33](/[CH3:32])\[C:37]#[C:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:57][CH:56]=1)[CH3:53]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 21597249(Z)-3-methyl-5-phenyl-pent-2-en-4-yn-1-ol

生成物 1

HCID 86583976(Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

1,1′-(azodicarbonyl) dipiperidine (0.504 g, 2.0 mmol) was added at 0° C. to a stirred solution of tributylphosphine (0.493 mL, 2.0 mmol), (Z)-3-methyl-5-phenyl-pent-2-en-4-yn-1-ol (0.172 g, 1.0 mmol) (J. Org. Chem. 1999, 64 (21), 7687-7692), and (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (0.262 g, 1.1 mmol) in dry benzene (20 mL), the mixture allowed to warm to room temperature, and stirring continued for 24 h. The resulting mixture was evaporated in vacuo, and the residue purified by flash column chromatography on silica gel (20% ethyl acetate in n-heptane eluent) to give (Z)-(S)-2-ethoxy-3-[4-(3-methyl-5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester as an oil; 0.267 g (68%).

後処理

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue purified by flash column chromatography on silica gel (20% ethyl acetate in n-heptane eluent)

出典と根拠

ORDレコード
ord-887474af8a8c42a49519969c348508ee
出典データセット
uspto-grants-2003_05
特許番号
US06569901B2

反応ノート

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