Hydrochloric Acid → HCID 53694139, compound

HRID 1417473Notes

Reaction equation

HRID 1417473 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[Na+].[CH2:31]([CH:38]([C:45]1[CH:53]=[C:52]2[C:48]([CH:49]=[CH:50][N:51]2[CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[CH:47][CH:46]=1)[C:39]([O:41]CC=C)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>C(Cl)Cl>[CH2:31]([CH:38]([C:45]1[CH:53]=[C:52]2[C:48]([CH:49]=[CH:50][N:51]2[CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[CH:47][CH:46]=1)[C:39]([OH:41])=[O:40])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 53993717HCID 53993717, compound

Product 1

HCID 53694139HCID 53694139, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 mg of tetrakistriphenylphosphine palladium, 7 mg of triphenylphosphine and 65 mg of sodium 2-ethylhexanoate were added to a solution of 104 mg of allyl 2-benzyl-2-(1-benzylindol-6-yl)acetate, as obtained in Example 65, in 5 ml of methylene chloride, and the resulting mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was acidified by the addition of a 3% aqueous solution of hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 5 g of silica gel with a 1:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 61 mg of the title compound as a solid material, melting at 148°-150° C.

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. additionwith a 1:1 v/v mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8021b01315f241d391bf9ee8091fc94e
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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