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

HRID 867120Notes

Reaction equation

HRID 867120 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 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-af612ee5b1b44eeb88933c106b480f2e
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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