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

HRID 977282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977282
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 145227763-(Hexadecylsulfanyl)-2-methoxypropan-1-OLAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9d51d0a35f934451b5c338e4c3470e2b
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614548

Notizen zur Reaktion

Wird geladen…