Tributylphosphine → (E)-(S)-ethyl 3-{4-[3-(4'-chloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

HRID 984318ノート

反応式

HRID 984318 の反応式
C(P(CCCC)CCCC)CCC.[CH2:14]([O:16][C@@H:17]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:15].[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41](/[C:44](/[CH3:48])=[CH:45]/[CH2:46]O)=[CH:40][CH:39]=2)=[CH:34][CH:33]=1>C1C=CC=CC=1.O.C(OCC)(=O)C>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH:43]=[CH:42][C:41](/[C:44](/[CH3:48])=[CH:45]/[CH2:46][O:30][C:27]3[CH:26]=[CH:25][C:24]([CH2:23][C@H:17]([O:16][CH2:14][CH3:15])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:29][CH:28]=3)=[CH:40][CH:39]=2)=[CH:36][CH:37]=1

参加物

7

反応物 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 69800319(E)-3-(4'-chloro-biphenyl-4-yl)-but-2-en-1-ol

生成物 1

HCID 86589947(E)-(S)-ethyl 3-{4-[3-(4'-chloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Azodicarboxylic dipiperidide (0.731 g, 2.9 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (0.71 ml, 0.58 g, 2.9 mmol), (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (0.483 g, 2.03 mmol) and (E)-3-(4′-chloro-biphenyl-4-yl)-but-2-en-1-ol (0.500 g, 1.93 mmol) in dry benzene (15 ml), the mixture warmed to room temperature, and stirred for 3 h. The resulting mixture was diluted with water and ethyl acetate (30 ml each), the aqueous layer collected and further extracted with ethyl acetate (30 ml). The organic layers were combined, washed with brine, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica (20% ethyl acetate in n-heptane eluent) to give (E)-(S)-ethyl 3-{4-[3-(4′-chloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate as a gum; 0.69 g (75%).

後処理

  1. customthe aqueous layer collected
  2. extractionfurther extracted with ethyl acetate (30 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was then purified by column chromatography on silica (20% ethyl acetate in n-heptane eluent)

出典と根拠

ORDレコード
ord-579d1d4d7168483f8c4e1b58cc66905c
出典データセット
uspto-grants-2005_03
特許番号
US06867218B2

反応ノート

読み込み中…