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

HRID 977282ノート

反応式

HRID 977282 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 145227763-(Hexadecylsulfanyl)-2-methoxypropan-1-OL収率 89.4%

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9d51d0a35f934451b5c338e4c3470e2b
出典データセット
uspto-grants-1997_03
特許番号
US05614548

反応ノート

読み込み中…