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Pyridine → (+/-)-2-Acetoxy-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

HRID 618846
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인쇄 미리보기

반응식

HRID 618846 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[O:3]1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:25]([O:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[O:3]1)(=[O:27])[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 21255848(+/-)2-Hydroxy-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

생성물 1

HCID 21255879(+/-)-2-Acetoxy-5-(p-Toluenesulfonyloxymethyl)-Tetrahydrofuran

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344
Dichloromethane
용매

실험 절차

To a stirring solution of (±)2-hydroxy-5-(p-toluenesulfonyloxymethyl)-tetrahydrofuran (example 58) (4.20 g, 15.44 mmol), pyridine (2.75 mL, 33.97 mmol) and DMAP (catalytic) in methylene chloride (100 mL) at rt was added acetic anhydride (2.91 mL, 30.88 mmol). After stirring the solution for 1 h, it was washed with water (50 mL), 1 N HCl (50 mL), saturated NaHCO3 (50 mL), dried (MgSO4) and concentrated to give the title compound as a 1:1 mixture of cis and trans isomers (4.85 g, 100%).

후처리

  1. washit was washed with water (50 mL), 1 N HCl (50 mL), saturated NaHCO3 (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f28d161c453046c39a25ebf8eb6ab477
출처 데이터셋
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05955610

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