Triphenylphosphine → HCID 140398710, compound

HRID 1419728Notes

Reaction equation

HRID 1419728 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:13]/[O:14][CH2:15][C:16]1[O:17][CH:18]=[C:19]([O:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20](=[O:22])[CH:21]=1)/[C:7]([O:9]CC=C)=[O:8].C(C(CCCC)C([O-])=O)C.[Na+:47].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:13]/[O:14][CH2:15][C:16]1[O:17][CH:18]=[C:19]([O:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:20](=[O:22])[CH:21]=1)/[C:7]([O-:9])=[O:8].[Na+:47]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 23672331Sodium 2-ethylhexanoateHCID 140398709HCID 140398709, compound

Product 1

HCID 140398710HCID 140398710, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of allyl (E)-2-(2-thienyl)-2-[(5-benzhydryloxy-4-pyranon-2-yl methoxy)imino]acetate (from Step 1, Example 2, 2.09 gm, 4.17 mmol), in a mixture of methylene chloride and ethyl acetate (25 ml: 55 ml) was treated with sodium 2-ethylhexanoate (693 mg, 4.17 mmol), triphenylphosphine (109 mg, 0.417 mmol) and Pd (PPh3)4 (193 mg, 0.167 mmol) and the mixture was stirred at room temperature for 5 hrs. The resulting precipitate was filtered, washed with a mixture of ether-ethyl acetate (1:1) and dried in vacuo to afford a white solid (2.0 gm, 99% yield).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with a mixture of ether-ethyl acetate (1:1)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b1ba82dd2c7d463a9aa754e99474daae
Source dataset
uspto-grants-1999_03
Patent number
US05888998

Reaction notes

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