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

HRID 714595

반응식

HRID 714595 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 86%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매

실험 절차

Dimethylaminopyridine (82 mg, 0.67 mmol) was added to a solution of (R)-propane-1,2-diol (5.17 g, 67.9 mmol) and trityl chloride (19.2 g 68.9 mmol) in DCM (200 mL) at 0° C. Triethylamine (23.5 mL, 168.6 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 (50 mL), washed with brine (50 mL), 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 (18.6 g, 86%) as a white solid. 1H NMR (DMSO-d6): δ 7.43-7.22 (m, 15H), 4.64 (d, 1H), 3.78 (m, 1H), 2.94 (dd, 1H), 2.70 (dd, 1H), 1.06 (d, 3H).

후처리

  1. washThe reaction mixture was washed with 1.0 N aq HCl (50 mL)
  2. washwashed with brine (50 mL)
  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-42051deea2e64016b841c62b0c3da4f3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187460B2

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