Water → HCID 59797428, compound

HRID 33796Notes

Reaction equation

HRID 33796 reaction equation
[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:16])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][O:21][CH3:22].O>CN(C=O)C>[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([O:16][CH2:20][O:21][CH3:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 597974464-Bromo-thianthren-1-ol

Product 1

HCID 59797428HCID 59797428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 4-Bromo-thianthren-1-ol (1.0 g, 3.21 mmol) in DMF (12 ml) was added NaH (60% dispersed in mineral oil, 0.23 g, 9.63 mmol) portionwise over 30 minutes and stirred for a further 30 minutes at this temperature. Chloromethylmethylether (0.26 g, 3.241 mmol) was then added and the reaction allowed to stir at room temperature for 2 hours. Water was added to the mixture which was then extracted using EtOAc (3×50 ml). The combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give a mild amber liquid. The crude residue was purified by flash chromatography (SiO2) (10:1, Hexanes/EtOAc) to give the title compound as a mild amber oil that crystallised upon standing (1.11 g, 97%). m/z (LC-MS, ESP):, RT=5.55 min, (M++1)=355.

Workup

  1. stirringto stir at room temperature for 2 hours
  2. extractionwas then extracted
  3. dry with materialThe combined organic extracts were then dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a mild amber liquid
  7. customThe crude residue was purified by flash chromatography (SiO2) (10:1, Hexanes/EtOAc)

Sources & evidence

ORD record
ord-30fec3e330a3440d8767dcf3ff793b3a
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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