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

HRID 618846
Notes
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Reaction equation

HRID 618846 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-f28d161c453046c39a25ebf8eb6ab477
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05955610

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes