Triphenylphosphine → ethyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoate

HRID 1363844Notes

Reaction equation

HRID 1363844 reaction equation
[SH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:46]([O:48][C:49](=[O:56])/[CH:50]=[C:51](\[CH3:55])/[CH2:52][CH2:53]O)[CH3:47]>C(OCC)(=O)C.C1COCC1>[CH2:46]([O:48][C:49](=[O:56])/[CH:50]=[C:51](\[CH3:55])/[CH2:52][CH2:53][S:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[N:4][N:3]=1)[CH3:47]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 59865204ethyl-(2E)-5-hydroxy-3-methylpent-2-enoateHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 59516418ethyl-(2E)-3-methyl-5-[(1-phenyl-1-H-tetrazol-5-yl)thio]pent-2-enoateYield 98.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

This reaction was performed with reference to the literature (Mitsunobu, O., Synthesis, 1981, 1-28.). 5-Mercapto-1-phenyltetrazole (16.30 g, 91.20 mmol), triphenylphosphine (27.30 g, 104 mmol) and diisopropyl azodicarboxylate (95%, 21.10 g, 104 mmol) were added to a THF (410 ml) solution of ethyl-(2E)-5-hydroxy-3-methylpent-2-enoate (13.80 g, 86.90 mmol) while ice cooling. The reaction solution was warmed to room temperature and stirred for four hours. After the reaction solution was diluted with ethyl acetate, it was washed with distilled water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=5:1) to obtain the title compound (27.16 g) as a white solid.

Workup

  1. custom, Synthesis, 1981, 1-28
  2. washwas washed with distilled water and brine
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a2e97dc0cc4e4011b8205dbfbc639a5d
Source dataset
uspto-grants-2011_02
Patent number
US07884128B2

Reaction notes

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