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

HRID 977282노트

반응식

HRID 977282 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21584188Chloroform methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9d51d0a35f934451b5c338e4c3470e2b
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614548

반응 노트

불러오는 중…