Sodium Hydroxide → 2-Fluorohex-5-ynoic acid

HRID 745681Notes

Reaction equation

HRID 745681 reaction equation
C([O:3][C:4](=[O:18])[C:5](C(=O)C)([F:14])[CH2:6][CH2:7][C:8]#[C:9][Si](C)(C)C)C.[O-]CC.[Na+].C(O)C.[OH-].[Na+]>C(O)C>[F:14][CH:5]([CH2:6][CH2:7][C:8]#[CH:9])[C:4]([OH:18])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 133930802-Acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl esterHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 130449502-Fluorohex-5-ynoic acidYield 101%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester (6.63 g) in ethanol (20 ml) was added 27 ml of 2.65M sodium ethoxide/ethanol. After 18 hours, 7 ml of 4N sodium hydroxide was added. After 6 hours, the solvent was removed by rotary evaporation and the residual materials partitioned between ethyl ether and dilute hydrochloric acid. The organic layer was dried (MgSO4) and the solvent removed by rotary evaporation to give an oil which was vacuum distilled to yield 3.2 g of 2-fluoro-5-hexynoic acid; b.p. 118°/14 mmHg.

Workup

  1. waitAfter 6 hours
  2. customthe solvent was removed by rotary evaporation
  3. customthe residual materials partitioned between ethyl ether and dilute hydrochloric acid
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed by rotary evaporation
  6. customto give an oil which
  7. distillationdistilled

Sources & evidence

ORD record
ord-6ab038b73ffc4af8ae5d6569a0a3e3a0
Source dataset
uspto-grants-1986_07
Patent number
US04599443

Reaction notes

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