2-Iodophenol → HCID 67033024, compound

HRID 876628Notes

Reaction equation

HRID 876628 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].S(C1C=CC(C)=CC=1)(O[CH2:13][CH2:14][C:15]([OH:18])([CH3:17])[CH3:16])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:13][CH2:14][C:15]([CH3:17])([OH:18])[CH3:16]

Participants

6

Reactant 3

HCID 107842-IodophenolHCID 10796Cesium carbonateHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol

Product 1

HCID 67033024HCID 67033024, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-iodophenol (6 g), 3-hydroxy-3-methylbutyl tosylate (7.4 g) and Cs2CO3 (13.3 g) in DMF (120 mL) was stirred at 0° C. for 2 h and at room temperature for 10 h. The mixture was diluted with EtOAc and washed with 1N HCl, saturated NaHCO3 aq., H2O, and brine, and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (Hexane/EtOAc=7/3) to obtain compound aa28-1 (8.02 g) as pale yellow oil.

Workup

  1. washwashed with 1N HCl, saturated NaHCO3 aq., H2O, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (Hexane/EtOAc=7/3)
  5. customto obtain compound aa28-1 (8.02 g) as pale yellow oil

Sources & evidence

ORD record
ord-13fc18d5454a463e883265f119a8e1be
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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