Trityl chloride → (2R)-1-(triphenylmethoxy)-2-propanol

HRID 717507ノート

反応式

HRID 717507 の反応式
[CH2:1]([OH:5])[C@H:2]([OH:4])[CH3:3].[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:6]([O:5][CH2:1][C@H:2]([OH:4])[CH3:3])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 259994R-(-)-1,2-Propanediol

生成物 1

HCID 11067110(2R)-1-(triphenylmethoxy)-2-propanol収率 84.4%

試薬・触媒・溶媒 2

HCID 218852-Dimethylaminopyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Dimethylaminopyridine (165 mg, 1.35 mmol) was added to a solution of (R)-propane-1,2-diol (10.3 g, 135.4 mmol) and trityl chloride (38.1 g 136.7 mmol) in DCM (400 mL) at 0° C. Triethylamine (47.2 mL, 338.4 mmol) was then added dropwise to this mixture. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was washed with 1.0 N aq HCl (200 mL), washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to give (R)-1-(trityloxy)propan-2-ol (36.4 g, 84%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.43-7.39 (m, 6H) 7.34-7.31 (m, 6H) 7.26-7.22 (m, 3H), 4.70 (d, 1H), 3.82-3.76 (m, 1H), 2.95-2.92 (dd, 1H), 2.70-2.67 (dd, 1H), 1.06 (d, 3H).

後処理

  1. washThe reaction mixture was washed with 1.0 N aq HCl (200 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-7a5d9940faf74fde91b7d560398f7b54
出典データセット
uspto-grants-2015_11
特許番号
US09193714B2

反応ノート

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