Tetrahydrofuran → HCID 86760308, compound

HRID 857312Notes

Reaction equation

HRID 857312 reaction equation
[Br:1][C:2]1[N:3]([CH2:19][CH2:20][CH2:21]C=O)[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:24]([CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:26][CH2:27][CH3:28])=[O:25].[CH2:49]1COCC1>CCCCCC.CCOC(C)=O>[Br:1][C:2]1[N:3]([CH2:19][CH2:20][CH2:21]/[CH:49]=[CH:29]/[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 21867456HCID 21867456, compound

Product 1

HCID 86760308HCID 86760308, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product obtained in Step 4 in 8 mL of THF was added 0.3 g (carbethoxymethylene)triphenylphosphorane. The reaction mixture was stirred for 2 hours at 50° C. and diluted with 20 mL of 10:1 hexane/EtOAc. The mixture was then filtered through a pad of silica gel and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluted with 9:1 hexane/EtOAc to give 0.2 g of the title compound as an oil.

Workup

  1. filtrationThe mixture was then filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography
  4. washeluted with 9:1 hexane/EtOAc

Sources & evidence

ORD record
ord-0cfdb63855c84bc6bd0445b2c7788a11
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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