Guaiacol → HCID 86612851, compound

HRID 1782024Notes

Reaction equation

HRID 1782024 reaction equation
[O:1]1[CH2:3][C@H:2]1COS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C@H:2]1[CH2:3][O:1]1

Participants

5

Reactant 3

HCID 460GuaiacolHCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 86612851HCID 86612851, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (777 mg, 3.0 mmol), 2-methoxyphenol (372.5 mg, 3.0 mmol) and Cs2CO3 (1.3 g, 4.0 mmol) in DMF was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit 40-60) to give subtitled compound (425 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-30% ethyl acetate in petroleum spirit 40-60)

Sources & evidence

ORD record
ord-68adbf71b21c4ac5a649a3d1da610519
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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