3-Chloro-1,2-propanediol → HCID 12800005, compound

HRID 2412617Notes

Reaction equation

HRID 2412617 reaction equation
[H-].[Na+].[CH2:3]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([C:22]([OH:24])=[O:23])=[CH:18][CH:19]=2)[NH:14]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl[CH2:26][CH:27]([OH:30])[CH2:28][OH:29]>CN(C)C=O>[CH2:3]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][C:17]([C:22]([O:24][CH2:26][CH:27]([OH:30])[CH2:28][OH:29])=[O:23])=[CH:18][CH:19]=2)[NH:14]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 24758Sodium hydrideHCID 12799968HCID 12799968, compound

Product 1

HCID 12800005HCID 12800005, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.32 g of a 50% oil dispersion) was added to a stirred solution of (RS)-2-(n-decyl)indoline-6-carboxylic acid (2 g; prepared as described hereinbefore in Example 57) in dry dimethylformamide (50 ml). When the addition was complete, the mixture was warmed on the steam bath for 1 hour with stirring, and 3-chloro-1,2-propanediol (0.8 g) was added. The mixture was warmed on the steam bath for 20 hours with stirring. The solvent was then evaporated to dryness and the residue was dissolved in dichloromethane. The solution in dichloromethane was washed with water, dried over magnesium sulphate and filtered, and the solvent evaporated to dryness to give an oil which slowly solidified. This solid was washed with petroleum ether (b.p. 60°-80° C.), filtered off and dried in air to give (RS)(RS)-2,3-dihydroxyprop-1-yl 2-(n-decyl)indoline-6-carboxylate (1.5 g), in the form of an off-white powder m.p. 102°-110° C.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was warmed on the steam bath for 1 hour
  3. temperatureThe mixture was warmed on the steam bath for 20 hours
  4. stirringwith stirring
  5. customThe solvent was then evaporated to dryness
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washThe solution in dichloromethane was washed with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent evaporated to dryness
  11. customto give an oil which
  12. washThis solid was washed with petroleum ether (b.p. 60°-80° C.)
  13. filtrationfiltered off
  14. customdried in air

Sources & evidence

ORD record
ord-2fecaa621492482dbfcc8727c8b52a33
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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