Methyl iodide → (+/-)-1-S-hexadecyl-2-O-methyl-3-O-tritylthioglycerol

HRID 977280Notes

Reaction equation

HRID 977280 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([CH2:21][O:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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].[H-].[Na+].[CH3:44]I>C1COCC1.O>[CH2:1]([S:17][CH2:18][CH:19]([CH2:21][O:22][C:23]([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)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:20][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

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 130028641-Hexadecylthio-3-trityloxy-2-propanol

Product 1

HCID 14522774(+/-)-1-S-hexadecyl-2-O-methyl-3-O-tritylthioglycerolYield 101.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.0 grams (0.01 mole) (±)-1-S-hexadecyl-3-O-tritylthioglycerol in 250 milliliters of THF was added to a slurry of 0.4 grams (0.014 mole) 80% NaH (oil dispersion) in 50 milliliters of THF and the reaction mixture stirred at room temperature for one hour. Then 1.4 gram (0.13 mole) of CH3I was added and the reaction allowed to proceed at room temperature for 24 hours. The reaction mixture was then diluted with 300 milliliters of distilled water and extracted twice with 200 milliliter portions of ether. The nonaqueous extracts were combined, dried over anhydrous sodium sulfate, filtered and removed in vacuo to provide 6.0 grams of crude product as an oil. 1H-NMR (CDCl3): delta, 0.7-1.7[m, 31H, (CH2)14CH3 ], 2.3-2.8(m, 4H, CH2 --S--CH2), 3.25(m, 5H, CH3O, CH--CH2 --O), 3.6-4.0(m, 1H, CH), 7.6-7.0[m, 15H, C(C6H5)3 ].

Workup

  1. waitto proceed at room temperature for 24 hours
  2. extractionextracted twice with 200 milliliter portions of ether
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-7fc21e71970948598b1eadaee890ab83
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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