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

HRID 984318노트

반응식

HRID 984318 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 241Benzene용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-579d1d4d7168483f8c4e1b58cc66905c
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867218B2

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