Trityl chloride → 1-Benzyl-3-tritylglycerol

HRID 482188

反応式

HRID 482188 の反応式
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][OH:13])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

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

生成物 1

HCID 36083721-Benzyl-3-tritylglycerol収率 72%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

rac-1-O-Benzylglycerol (5.37 g, 29.5 mmol), trityl chloride (8.31 g, 29.8 mmol) and anhydrous pyridine (35 ml) were placed in a flame-dried 200 ml round-bottomed flask. The reaction mixture was stirred under anhydrous conditions at room temperature for two days. The precipitate which formed was filtered before H2O and ether were added. The ether layer was extracted with H2O, 1N HCl and H2O, and dried (MgSO4). The solvent was removed by reduced pressure to provide a viscous yellow oil. The crude product was purified by column chromatography (180 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 3:1) to yield pure compound 12, rac-1-O-benzyl-3-O-tritylglycerol (9.00 g, 72% yield).

後処理

  1. customThe precipitate which formed
  2. filtrationwas filtered before H2O and ether
  3. additionwere added
  4. extractionThe ether layer was extracted with H2O, 1N HCl and H2O
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by reduced pressure
  7. customto provide a viscous yellow oil
  8. customThe crude product was purified by column chromatography (180 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 3:1)

出典と根拠

ORDレコード
ord-f0c920e07153439cbef18857eeeb09e5
出典データセット
uspto-grants-1998_08
特許番号
US05795561

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