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

HRID 984318Notes

Reaction equation

HRID 984318 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-579d1d4d7168483f8c4e1b58cc66905c
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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