Tetrahydrofuran → HCID 67323793, compound

HRID 1616920Notes

Reaction equation

HRID 1616920 reaction equation
[H-].[Na+].[C:3](CP(=O)(OCC)OCC)#[N:4].[H][H].[CH2:16]([O:18][C:19](=[O:33])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[C:30](=O)[CH3:31])[CH3:17].[CH2:34]1COCC1>>[CH2:16]([O:18][C:19](=[O:33])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[C:30]([CH3:34])=[CH:31][C:3]#[N:4])[CH3:17]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 4695677HCID 4695677, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67323793HCID 67323793, compound

Conditions

Temperature
0 °C

Procedure

To a slurry of Sodium hydride, 60% disp. in mineral oil (7.44 g, 0.186 mol) in Tetrahydrofuran (200 mL, 2 mol) was added and a solution of diethyl cyanomethylphosphonate (30.0 mL, 0.186 mol) in THF (50 mL) slowly, hydrogen was released. After addition and 10 minutes at RT the reaction was cooled at 0° C. and a mixture of (2-acetyl-5-methoxy-phenoxy)-acetic acid ethyl ester (44.6 g, 0.177 mol) in tetrahydrofuran (150 mL) was added dropwise. After 2 hr at 0° C., the reaction was transferred into ice/water and extracted with diethylether. The ether layer was washed with brine, dried, filtered and concentrated. The product was used in the next reaction step without further purification.

Workup

  1. additionAfter addition and 10 minutes at RT the reaction
  2. additionwas added dropwise
  3. extractionextracted with diethylether
  4. washThe ether layer was washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-ede45a5a0bb34e248e08d7ec0d2f788c
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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