Tetrahydrofuran → HCID 88322125, compound

HRID 726935Notes

Reaction equation

HRID 726935 reaction equation
[CH2:1]([CH:17]([OH:38])[CH:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:19]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][CH3:16].O1CCCC1.[CH3:44][S-:45].[Na+].C(OCC)(=O)C>CCCCCC.C(Cl)(Cl)Cl>[CH2:1]([CH:17]([OH:38])[CH:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:19][S:45][CH3:44])[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][CH3:16]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolate2×HCID 88153519HCID 88153519, compound

Product 1

HCID 88322125HCID 88322125, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

Racemic 1,2-O-dihexadecyl-3-bromo-1,2-propanediol (from Step 1), 2.0 g (3.3 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 2.33 g (33.2 mmoles) of sodium thiomethoxide powder and the reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC (silica gel, 5% ethyl acetate in hexane) and an additional 490 mg (7 mmoles) of sodium thiomethoxide was added to the reaction. After an additional 3 hr, 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 was washed twice with 25 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. The crude product was purified by column chromatography on a silica gel 60 (E. Merck, Germany) column using a step gradient of 0 to 10% ethyl acetate in hexane. The fractions collected were screened by TLC. Those fractions containing pure product were pooled and concentrated to afford 1,2-O-dihexadecyl-3-methylthio-1,2-propanediol in 90% yield.

Workup

  1. customequipped with a magnetic stir bar
  2. waitAfter an additional 3 hr
  3. filtrationthe mixture was filtered
  4. washthe filtrate was washed with 50 ml tetrahydrofuran
  5. concentrationThe combined filtrates were concentrated under vacuum
  6. customa rotary evaporator
  7. customto afford a yellow residue
  8. washthe organic solution was washed twice with 25 ml of a concentrated solution of sodium bicarbonate
  9. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  10. concentrationconcentrated on a rotary evaporator under vacuum
  11. customto afford the crude product as a pale yellow oily residue
  12. customThe crude product was purified by column chromatography on a silica gel 60 (E. Merck, Germany) column
  13. customThe fractions collected
  14. additionThose fractions containing pure product
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-e029f27a055e439a86572581e5ef3d9b
Source dataset
uspto-grants-1998_01
Patent number
US05711964

Reaction notes

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