Sodium hydride → HCID 57429710, compound

HRID 1455559Notes

Reaction equation

HRID 1455559 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5](P(OCC)(OCC)=O)[F:6])[CH3:2].[H-].[Na+].O=[C:19]1[CH:26]2[CH2:27][C:22]3([O:29][C:30](=[O:36])[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:23][CH:24]([CH2:28][CH:20]1[CH2:21]3)[CH2:25]2>C1COCC1>[F:6][C:5](=[C:25]1[CH:26]2[CH2:27][C:22]3([O:29][C:30](=[O:36])[CH2:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:21][CH:20]([CH2:28][CH:24]1[CH2:23]3)[CH2:19]2)[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 57429709HCID 57429709, compound

Product 1

HCID 57429710HCID 57429710, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.48 ml of (diethoxy-phosphoryl)-fluoro-acetic acid ethyl ester are added dropwise to a suspension of 317 mg of NaH (55% in mineral oil) in 30 ml of THF at 0°. The mixture obtained is stirred, 1.37 g of 3,3-dimethyl-butyric acid 4-oxo-adamantan-1-yl ester in 10 ml of THF are added slowly and the mixture obtained is stirred at RT overnight. The mixture obtained is diluted with EtAc and the diluted mixture obtained is washed with 1M aqueous NaH2PO4 and saturated aqueous NaHCO3 solution. The organic layer obtained is dried, solvent is evaporated and the evaporation residue obtained is subjected to chromatography on silica gel. 3,3-Dimethyl-butyric acid 4-(fluoro-ethoxycarbonyl-methylene)-adamantan-1-yl ester is obtained in the form of an oil.

Workup

  1. customThe mixture obtained
  2. customthe mixture obtained
  3. stirringis stirred at RT overnight
  4. customThe mixture obtained
  5. additionis diluted with EtAc
  6. customthe diluted mixture obtained
  7. washis washed with 1M aqueous NaH2PO4 and saturated aqueous NaHCO3 solution
  8. customThe organic layer obtained
  9. customis dried
  10. customsolvent is evaporated
  11. customthe evaporation residue obtained

Sources & evidence

ORD record
ord-8053d0bc80bc40b7934b277b3f00cddb
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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