L-Pyroglutamic Acid → 4-Phenoxybut-2-yn-1-ol

HRID 652117Notes

Reaction equation

HRID 652117 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]#[C:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C(=O)CC[C@H]1C(O)=O>C(O)C>[O:12]([CH2:11][C:10]#[C:9][CH2:8][OH:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 19849494HCID 19849494, compound

Product 1

HCID 160466794-Phenoxybut-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2 g (0.008 mol) of 4-phenoxybut-2-yn-1-ol tetrahydropyranyl ether in 20 ml of 96% ethanol, there was added 1.02 g (0.004 mol) of Pyr/PTS. The reaction mixture was stirred for 2 hours at 55° C.; the solvent was then removed in vacuo and the residue diluted with 20 ml of water and extracted with methylene chloride. The combined extracts were dried and evaporated in vacuo. The residue was purified by column chromatography on 30 g of silica gel, using hexane-ethyl acetate (90:10) as eluant, to yield 4-phenoxybut-2-yn-1-ol, as an oil.

Workup

  1. customthe solvent was then removed in vacuo
  2. additionthe residue diluted with 20 ml of water
  3. extractionextracted with methylene chloride
  4. customThe combined extracts were dried
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on 30 g of silica gel

Sources & evidence

ORD record
ord-7185982d1a314bbf87641521d30effbe
Source dataset
uspto-grants-1987_06
Patent number
US04670465

Reaction notes

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