Chloroform → 3-(Hexadecylsulfanyl)-2-methoxypropan-1-ol

HRID 977282Notes

Reaction equation

HRID 977282 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][O:23]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:20][CH3:21])[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(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl>C(Cl)(Cl)Cl.CO>[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][OH:23])[O:20][CH3:21])[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

5

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 14522774(+/-)-1-S-hexadecyl-2-O-methyl-3-O-tritylthioglycerol

Product 1

HCID 145227763-(Hexadecylsulfanyl)-2-methoxypropan-1-olYield 89.4%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of 6.0 grams (0.01 mole) of (±)-1-S-hexadecyl-2-O-methyl-3-O-tritylthioglycerol in 100 milliliters of chloroform:methanol (3:1) was added 0.2 gram of p-toleunesulfonic acid and the reaction stirred at room temperature for 24 hours. The reaction mixture was neutralized with 1.0 gram of sodium bicarbonate and then extracted three times with 200 milliliter portions of water. The nonaqueous layer was separated and the solvent removed in vacuo to give the crude product as an oil. Silica gel chromatography (CHCl3 eluent) provided 3.1 grams (89%) of pure product as a semi-waxy solid. 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 28H, (CH2)14 ], 2.58 (m, 2H, --S--CH2), 2.62 (m, 2H, CH--CH2 --S--), 3.40(m, 1H, CH), 3.44(s, 3H, CH3 --O--), 3.75(m, 2H, CH2 --OH).

Workup

  1. extractionextracted three times with 200 milliliter portions of water
  2. customThe nonaqueous layer was separated
  3. customthe solvent removed in vacuo
  4. customto give the crude product as an oil

Sources & evidence

ORD record
ord-9d51d0a35f934451b5c338e4c3470e2b
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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