Chloroform → Sodium Chloride

HRID 28205Notes

Reaction equation

HRID 28205 reaction equation
[OH-:1].[Na+:2].O[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][S:14][CH:13]1[CH2:18][CH2:19][CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=1.C(Cl)(Cl)[Cl:33]>CO.O>[OH:1][CH:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][S:14][CH:13]1[CH2:18][CH2:19][CH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.[Na+:2].[Cl-:33]

Participants

7

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 23468107HCID 23468107, compound

Product 2

HCID 5234Sodium ChlorideHCID 9908595L-644,698

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydroxide solution (5 N, 2.5 ml., 12.5 mmol.) is added dropwise to a stirred mixture of ethyl 4-{3-[3-(hydroxyoctyl)-4-oxo-2-thiazolidinyl]propyl}benzoate (2.80 g., 6.64 mmol.) in aqueous methanol (25 ml. methanol plus 5 ml. water) maintained at 0° C. The resulting mixture is allowed to warm to room temperature and stirred for 3 hours. Then, the reaction mixture is diluted with water, and extracted with ether. The aqueous phase is separated, acidified with 2 N hydrochloric acid (10 ml.), and extracted with ether. This ethereal extract is washed with water, dried over anhydrous magnesium sulfate, concentrated in vacuo to yield an oil residue. The oil residue is then applied to a silica gel column (75 g.) with chloroform. Elution with chloroform-acetic acid (25:1; v:v; 410 ml.) gives impure material. Continued elution with the same eluant (420 ml.) provides the desired title compound as a viscous pale yellow oil, ir (NaCl) 1700, 1665 cm- 1, pmr (CDCl3) δ0.92 (3H, t), 3.60 (2H, s), 4.72 (1H, m), 7.30 (2H, d), 8.08 (2H, d).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with ether
  3. customThe aqueous phase is separated
  4. extractionextracted with ether
  5. extractionThis ethereal extract
  6. washis washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield an oil residue
  10. washElution with chloroform-acetic acid (25:1; v:v; 410 ml.)
  11. customgives impure material
  12. washelution with the same eluant (420 ml.)

Sources & evidence

ORD record
ord-98e469cd619040509b224c6f001ed038
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

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