p-Toluenesulfonic acid monohydrate → HCID 10678360, compound

HRID 345642Notes

Reaction equation

HRID 345642 reaction equation
O.C1(C)C=CC(S(O)(=O)=[O:9])=CC=1.[N+:13]([CH2:16][C@@H:17]1[CH2:21][C@H:20](CC([O-])=O)[CH:19]=[CH:18]1)([O-:15])=[O:14]>CO>[N+:13]([CH2:16][C@H:17]1[CH2:21][C@@H:20]([OH:9])[CH:19]=[CH:18]1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18647344HCID 18647344, compound

Product 1

HCID 10678360HCID 10678360, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 5 mL round-bottom flask is added at room temperature p-toluenesulphonic acid monohydrate (0.01 g, 0.053 mmol), methanol (8 mL) and (1R-cis)-4-nitromethyl-2-cyclopentene -acetate as prepared in Example 10 (0.20 g, 1.1 mmol) and the resulting solution is stirred overnight. The crude reaction mixture is loaded on a silica column (32 μm-63 μm) and purified by flash chromatography by eluting with 20% ethyl acetate/hexane. The fractions containing the product (Rf=0.3) are combined and are concentrated in vacuo to give (1R-cis)-4-nitromethyl-2-cyclopenten-1-ol as a clear oil which exhibited the following physical data: MS(CI) m/z=126 [C6H8NO2 +, Loss of H2O followed by rapid protonation]; and [α]D20 =+4.8° (c=0.16, CHCl3).

Workup

  1. customThe crude reaction mixture
  2. custompurified by flash chromatography
  3. washby eluting with 20% ethyl acetate/hexane
  4. additionThe fractions containing the product (Rf=0.3)
  5. concentrationare concentrated in vacuo

Sources & evidence

ORD record
ord-2039386b8c1841eab0c28fd44ac11c32
Source dataset
uspto-grants-1991_10
Patent number
US05057630

Reaction notes

Loading…