Diazoethane → HCID 54001360, compound

HRID 2397627Notes

Reaction equation

HRID 2397627 reaction equation
[N+](=[CH:3][CH3:4])=[N-].[OH:5][CH:6]([CH2:25][O:26][CH2:27][CH2:28][CH3:29])[CH2:7][CH2:8][N:9]1[C:13](=[O:14])[CH2:12][S:11](=[O:15])[CH:10]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]>CCOCC>[OH:5][CH:6]([CH2:25][O:26][CH2:27][CH2:28][CH3:29])[CH2:7][CH2:8][N:9]1[C:13](=[O:14])[CH2:12][S:11](=[O:15])[CH:10]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:3][CH3:4])=[O:23]

Participants

4

Reactant 2

HCID 70695DiazoethaneHCID 21436325HCID 21436325, compound

Product 1

HCID 54001360HCID 54001360, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazoethane (approximately 3.4 g., 0.06 mole) in ether (100 ml.) is slowly added to a solution of 7-[3-(3-hydroxy-4-propoxybutyl)-1,4-dioxo-2-thiazolidinyl]heptanoic acid (11.3 g., 0.03 mole) in ether (50 ml.) with stirring and cooling (0° to 5° C.). The resulting solution is allowed to warm to and stand at room temperature for 4 hours. After destroying excess diazoethane with acetic acid, the reaction solution is washed with 5% sodium bicarbonate solution and water, dried over sodium sulfate, and filtered. In vacuo evaporation of the filtrate leaves the title compound as an essentially colorless, viscous oil.

Workup

  1. temperaturecooling (0° to 5° C.)
  2. temperatureto warm to and
  3. customAfter destroying excess diazoethane with acetic acid
  4. washthe reaction solution is washed with 5% sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customIn vacuo evaporation of the filtrate

Sources & evidence

ORD record
ord-f6f88574405149278700c185cafcc025
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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