Diazomethane → Methyl 7-[2-(3-Hydroxy-4-propoxybutyl)-1,4-dioxo-3-thiazolidinyl]heptanoate

HRID 1439406Notes

Reaction equation

HRID 1439406 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH:5]([CH2:24][O:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:11](=[O:22])[CH2:10][S:9]1=[O:23]>CCOCC>[OH:4][CH:5]([CH2:24][O:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:3])=[O:20])[C:11](=[O:22])[CH2:10][S:9]1=[O:23]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 203173927-[2-(3-Hydroxy-4-propoxybutyl)-1,4-dioxo-3-thiazolidinyl]heptanoic Acid

Product 1

HCID 20317399Methyl 7-[2-(3-Hydroxy-4-propoxybutyl)-1,4-dioxo-3-thiazolidinyl]heptanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is slowly added to a solution of 7-[2-(3-hydroxy-4-propoxybutyl)-1,4-dioxo-3-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 up at room temperature for 4 hours. After destroying excess diazomethane 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 diazomethane 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-56dedb3a213544daa5a4b371db0dd71b
Source dataset
uspto-grants-1977_11
Patent number
US04059587

Reaction notes

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