3-Chloro-1,2-propanediol → HCID 21390347, compound

HRID 462045Notes

Reaction equation

HRID 462045 reaction equation
[OH-].[K+].[CH2:3]([N:6]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:7]1=[O:8])[CH:4]=[CH2:5].[CH2:18]([OH:23])[CH:19]([OH:22])[CH2:20]Cl>CO>[CH2:3]([N:6]1[C:16]2[C:11](=[C:12]([O:17][CH2:20][CH:19]([OH:22])[CH2:18][OH:23])[CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][C:7]1=[O:8])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 14797Potassium HydroxideHCID 20438747HCID 20438747, compound

Product 1

HCID 21390347HCID 21390347, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.4 g of potassium hydroxide was dissolved in 40 ml of methanol, and 1.0 g of 1-allyl-5-hydroxy-3,4-dihydrocarbostyril and 1.5 g of glycerol α-monochlorohydrin were added to the resulting solution followed by refluxing the mixture for 6 hours. The mixture was then worked up in the same manner as described in Example 3 and recrystallized from ethyl acetate to give 0.6 g of 1-allyl-5-(2,3-dihydroxy)propoxy-3,4-dihydrocarbostyril as a colorless amorphous solid having a melting point of 96° - 97.5° C.

Workup

  1. temperatureby refluxing the mixture for 6 hours
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e096a8414fd941a0ba0ddff13af478ee
Source dataset
uspto-grants-1977_12
Patent number
US04065456

Reaction notes

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