Water → HCID 12799963, compound

HRID 2412647Notes

Reaction equation

HRID 2412647 reaction equation
[CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O-:23])=[O:22])[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Na+].Cl[CH2:26][CH:27]([OH:30])[CH2:28][OH:29].[I-].[K+].O>COCCOCCOC>[CH2:1]([C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([C:21]([O:23][CH2:26][CH:27]([OH:30])[CH2:28][OH:29])=[O:22])[CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 72903-Chloro-1,2-propanediolHCID 23682493HCID 23682493, compound

Product 1

HCID 12799963HCID 12799963, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of sodium 2-(n-undecyl)indole-6-carboxylate (5.0 g) and 3-chloro-1,2-propanediol (1.64 g) in diglyme (50 ml) was refluxed for 30 minutes. Potassium iodide (2.5 g) was added and the mixture refluxed for 48 hours. The mixture was cooled, water (50 ml) was added and the resulting emulsion was extracted with dichloromethane (2×100 ml). The combined extracts were dried over anhydrous magnesium sulphate, filtered, and the solvent evaporated to dryness. The solid residue was recrystallised from cyclohexane, filtered off and dried to give (RS)-2,3-dihydroxyprop-1-yl 2-(n-undecyl)indole-6-carboxylate (1.5 g) in the form of a white solid, m.p. 110°-112° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe mixture refluxed for 48 hours
  3. temperatureThe mixture was cooled
  4. extractionthe resulting emulsion was extracted with dichloromethane (2×100 ml)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated to dryness
  8. customThe solid residue was recrystallised from cyclohexane
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-5a26de2c05aa4450b47bf7e68e9bfaca
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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