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

HRID 717507

반응식

HRID 717507 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 11067110(2R)-1-(triphenylmethoxy)-2-propanol수율 84.4%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7a5d9940faf74fde91b7d560398f7b54
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193714B2

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