Tributylphosphine → HCID 11320149, compound

HRID 1353191Notes

Reaction equation

HRID 1353191 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].[CH2:31]([O:33][C:34](=[O:68])[C@@H:35]([O:65][CH2:66][CH3:67])[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44]/[CH:45]=[C:46](/[C:48]2[CH:53]=[CH:52][C:51]([C:54]3[CH:59]=[CH:58][C:57](/[C:60](/[CH3:64])=[CH:61]/[CH2:62]O)=[CH:56][CH:55]=3)=[CH:50][CH:49]=2)\[CH3:47])=[CH:39][CH:38]=1)[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][CH2:62]/[CH:61]=[C:60](/[C:57]2[CH:56]=[CH:55][C:54]([C:51]3[CH:52]=[CH:53][C:48](/[C:46](/[CH3:47])=[CH:45]/[CH2:44][O:43][C:40]4[CH:39]=[CH:38][C:37]([CH2:36][C@H:35]([O:65][CH2:66][CH3:67])[C:34]([O:33][CH2:31][CH3:32])=[O:68])=[CH:42][CH:41]=4)=[CH:49][CH:50]=3)=[CH:59][CH:58]=2)\[CH3:64])=[CH:28][CH:29]=1)[CH3:22]

Participants

7

Reactant 3

HCID 13831TributylphosphineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 11249305HCID 11249305, compound

Product 1

HCID 11320149HCID 11320149, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (0.50 g, 1.89 mmol) was added at 0–5° C. to a stirred solution of tributylphosphine (0.37 mL, 1.89 mmol), (S)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)-propionate (0.32 g, 1.32 mmol) and (E)(E)(S) 2-ethoxy-3-(4-{3-[4′-{3-hydroxy-1-methyl-propenyl)-biphenyl-4-yl]-but-2-enyloxy}-phenyl)-propionic acid ethyl ester (0.65 g, 1.26 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 to give 580 mg (63%) of the title compound.

Workup

  1. customthe aqueous layer collected
  2. extractionfurther extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-fd1a7473f526485087f7b178e1a11f81
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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