Trityl chloride → 1-Benzyl-3-tritylglycerol

HRID 1690802

反応式

HRID 1690802 の反応式
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:28]([O:35][CH2:36][CH:37]([OH:40])[CH2:38][OH:39])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)(C)(C)C>[CH2:28]([O:35][CH2:36][CH:37]([CH2:38][O:39][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:40])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 980723-(Benzyloxy)-1,2-propanediol

生成物 1

HCID 36083721-Benzyl-3-tritylglycerol収率 80.1%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒2 回

実験手順

To a stirred suspension of triphenylmethyl chloride (59.6 g, 0.21 mol) and triethylamine (32.6 mL, 0.23 mol) in tert-butyl alcohol (80 mL) at 60° C. was added a solution of 1-benzyloxy-2,3-propanediol (37.1 g, 0.20 mol) in tert-butyl alcohol (20 mL). The reaction was heated at reflux for 24 hours. The reaction mixture was evaporated to dryness, then purified using flash chromatography (0 to 30% EtOAc in hexanes) to afford the title compound (68 g, 75%) as an oil. m/z not found, r.t.=4.32 mins. 1H NMR (400 MHz; CDCl3) δ 7.46-7.41 (6H, m), 7.36-7.22 (14H, m), 4.52 (2H, s), 4.02-3.95 (1H, m), 3.63-3.54 (2H, m), 3.26-3.18 (2H, m), 2.40 (1H, s).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 hours
  3. customThe reaction mixture was evaporated to dryness
  4. custompurified

出典と根拠

ORDレコード
ord-212bbfecd0f94c7b83196cf3f8a3dbc2
出典データセット
uspto-grants-2012_04
特許番号
US08153651B2

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