Trityl chloride → 1-Hexadecylthio-3-trityloxy-2-propanol

HRID 977279Notes

Reaction equation

HRID 977279 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([CH2:21][OH:22])[OH:20])[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].[C:23]1([C:29](Cl)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH2:1]([S:17][CH2:18][CH:19]([CH2:21][O:22][C:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[OH:20])[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

4

Reactant 2

HCID 6456Trityl chlorideHCID 13002863HCID 13002863, compound

Product 1

HCID 130028641-Hexadecylthio-3-trityloxy-2-propanolYield 98.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar and drying tube, a solution of 70 grams (0.2 mole) (±)-1-S-hexadecylthioglycerol in 300 milliliters of pyridine was added, followed by the addition of 76.0 grams (0.27 mole) triphenylmethyl chloride. The reaction mixture was stirred at room temperature. After 36 hours, the pyridine was removed in vacuo and the resulting oil was dissolved in 450 milliliters of CHCl3. The solution was extracted twice with 500 milliliter portions of 5% HCl, twice with 500 milliliter portions of water and the nonaqueous solution was dried over anhydrous sodium sulfate. The drying agent was filtered, the solvent was removed in vacuo, the residue was dissolved in 500 milliliters of hexanes, and the solution was placed at -5° Centigrade for 24 hours. The resulting precipitate was redissolved in 500 milliliters of acetone and reprecipitated as before. The final precipitate was filtered and dried under vacuum to give 113 grams (94%) of product, (mp 61°-62° Centigrade). 1H-NMR (CDCl3): delta, 0.7-1.7[m, 31H, (CH2)14CH3 ], 2.3-2.8(m, 4H, CH2 --S--CH2), 3.25[d, 2H, CH2 --O--C(C6H5)3 ], 3.6-4.0(m, 1H, CH2 --CH--CH2), 7.0-7.6[m, 15H, C(C6H5)3 ].

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customdrying tube
  3. customthe pyridine was removed in vacuo
  4. dissolutionthe resulting oil was dissolved in 450 milliliters of CHCl3
  5. extractionThe solution was extracted twice with 500 milliliter portions of 5% HCl, twice with 500 milliliter portions of water
  6. dry with materialthe nonaqueous solution was dried over anhydrous sodium sulfate
  7. filtrationThe drying agent was filtered
  8. customthe solvent was removed in vacuo
  9. dissolutionthe residue was dissolved in 500 milliliters of hexanes
  10. customwas placed at -5°
  11. customfor 24 hours
  12. dissolutionThe resulting precipitate was redissolved in 500 milliliters of acetone
  13. customreprecipitated as before
  14. filtrationThe final precipitate was filtered
  15. customdried under vacuum

Sources & evidence

ORD record
ord-5b8652651358457292884a5125d4c55c
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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