Tetrahydrofuran → 1O-octadecyl-2-O-benzyl-3-methylthio-1,2-propanediol

HRID 726937Notes

Reaction equation

HRID 726937 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:22]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O1CCCC1.[CH3:37][S-:38].[Na+].C(OCC)(=O)C>CCCCCC.C(Cl)(Cl)Cl>[CH2:1]([O:19][CH2:20][CH:21]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:22][S:38][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 53871789HCID 53871789, compound

Product 1

HCID 544168751O-octadecyl-2-O-benzyl-3-methylthio-1,2-propanediolYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

Racemic 1-O-octadecyl-2-O-benzyl-3-bromo-1,2-propanediol, 1.99 g (4.0 mmoles), was dissolved into 100 ml of dry tetrahydrofuran in a 250 ml round bottom flask equipped with a magnetic stir bar. To this solution was added 2.8 g (40.0 mmoles) of sodium thiomethoxide powder and the reaction mixture stirred for 4.5 hours at room temperature. The reaction was monitored by TLC (silica gel, 5% ethyl acetate in hexane; Rf=0.51). The mixture was filtered and the filtrate was washed with 50 ml tetrahydrofuran. The combined filtrates were concentrated under vacuum using a rotary evaporator to afford a yellow residue. This residue was dissolved into 50 ml chloroform and the organic solution washed twice with 30 ml of a concentrated solution of sodium bicarbonate. The organic phase was then dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator under vacuum to afford the crude product as a pale yellow oily residue. This crude product was purified by chromatography on silica gel 60 (E. Merck, Germany) using a step gradient of 0 to 10% ethyl acetate in hexane. The fractions collected were screened by TLC. Those fractions containing pure product (silica gel, 5% ethyl acetate in hexane, Rf=0.51) were pooled and concentrated to afford 1-O-octadecyl-2-O-benzyl-3-methylthio-1,2-propanediol in 90% yield.

Workup

  1. customequipped with a magnetic stir bar
  2. filtrationThe mixture was filtered
  3. washthe filtrate was washed with 50 ml tetrahydrofuran
  4. concentrationThe combined filtrates were concentrated under vacuum
  5. customa rotary evaporator
  6. customto afford a yellow residue
  7. washthe organic solution washed twice with 30 ml of a concentrated solution of sodium bicarbonate
  8. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  9. concentrationconcentrated on a rotary evaporator under vacuum
  10. customto afford the crude product as a pale yellow oily residue
  11. customThis crude product was purified by chromatography on silica gel 60 (E. Merck, Germany)
  12. customThe fractions collected
  13. additionThose fractions containing pure product (silica gel, 5% ethyl acetate in hexane, Rf=0.51)
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-4baf7596998444c8bc9aa12a6f0d2d37
Source dataset
uspto-grants-1998_01
Patent number
US05711964

Reaction notes

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