Stearoyl chloride → HCID 20377403, compound

HRID 2052350Notes

Reaction equation

HRID 2052350 reaction equation
C(O)(=O)C.[OH:5][CH:6]1[CH2:9][NH:8][CH2:7]1.[C:10](Cl)(=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>N1C=CC=CC=1>[C:10]([N:8]1[CH2:9][CH:6]([OH:5])[CH2:7]1)(=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 8212Stearoyl chlorideHCID 70591891HCID 70591891, compound

Product 1

HCID 20377403HCID 20377403, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Stir a suspension of 6.31 g of 3-hydroxyazetidine acetate in 150 ml dry pyridine until a solution results. Add 15.8 g stearoyl chloride at room temperature during ten minutes and stir for 21 hours at room temperature. Pour into 450 ml of an ice-water mixture, and extract once with 300 ml ethyl ether and then twice with 250 ml portions chloroform. Wash the combined extracts with three 150 ml portions of water, dry over anhydrous sodium sulfate and remove the solvents in vacuo. Stir the residue in 250 ml hexane and filter the resultant solid. Recrystallization from hexane affords pure 1-octadecanoyl-3-hydroxyazetidine, m.p. 86°-87.5° C.

Workup

  1. customresults
  2. stirringstir for 21 hours at room temperature
  3. extractionextract once with 300 ml ethyl ether
  4. washWash the combined extracts with three 150 ml portions of water
  5. dry with materialdry over anhydrous sodium sulfate
  6. customremove the solvents in vacuo
  7. stirringStir the residue in 250 ml hexane
  8. filtrationfilter the resultant solid
  9. customRecrystallization from hexane

Sources & evidence

ORD record
ord-2052934286b442f69b6351229f65e666
Source dataset
uspto-grants-1980_01
Patent number
US04183923

Reaction notes

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