Tributylphosphine → HCID 86588415, compound

HRID 1353189Notes

Reaction equation

HRID 1353189 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].[Si:31]([CH2:38][O:39][CH2:40]/[CH:41]=[C:42](/[C:44]1[CH:49]=[CH:48][C:47]([C:50]2[CH:55]=[CH:54][C:53](/[C:56](/[CH3:60])=[CH:57]/[CH2:58]O)=[CH:52][CH:51]=2)=[CH:46][CH:45]=1)\[CH3:43])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C1COCC1.O.C(OCC)(=O)C>[CH2:21]([O:20][C:18](=[O:19])[C@@H:17]([O:16][CH2:14][CH3:15])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:58]/[CH:57]=[C:56](/[C:53]2[CH:54]=[CH:55][C:50]([C:47]3[CH:48]=[CH:49][C:44](/[C:42](/[CH3:43])=[CH:41]/[CH2:40][O:39][CH2:38][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[CH:45][CH:46]=3)=[CH:51][CH:52]=2)\[CH3:60])=[CH:28][CH:29]=1)[CH3:22]

Participants

7

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 86588413HCID 86588413, compound

Product 1

HCID 86588415HCID 86588415, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (0.91 g, 3.62 mmol) was added at 0–5° C. to a stirred solution of tributylphosphine (0.89 mL, 3.62 mmol), (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (0.60 g, 2.53 mmol) and (E)(E) 3-(4′-{3-[(tert-butyidimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-en-1-ol (1.02 g, 2.41 mmol) in dry THF (15 ml). The mixture was warmed to room temperature, and stirred for 18 h. The resulting mixture was diluted with water and ethyl acetate, the aqueous layer collected and further extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica using heptane/ethyl acetate (4:1) as eluent to give 1.18 g (76%) of (E)(E)(S) 3-{4-[3-(4′-{3-[(tert-butyldimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester.

Workup

  1. customthe aqueous layer collected
  2. extractionfurther extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was then purified by column chromatography on silica

Sources & evidence

ORD record
ord-30195b2a460f4f44a6824c9eada97dd2
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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