1,2-Dichloroethane → HCID 57803565, compound

HRID 2102988Notes

Reaction equation

HRID 2102988 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:18])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[S:11][CH2:10][CH2:9][C:8]2=[O:17].Cl[CH2:20][CH2:21]Cl.[H-].[Na+].O>CN(C=O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:18])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[S:11][CH2:10][C:9]1([CH2:21][CH2:20]1)[C:8]2=[O:17]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 24758Sodium hydrideHCID 69054868HCID 69054868, compound2×

Product 1

HCID 57803565HCID 57803565, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methoxymethoxy-5,7,8-trimethyl-2,3-dihydro-4H-thiochromen-4-one (23 mg) was dissolved in anhydrous DMF (5 mL) and treated with 1,2-dichloroethane (6.8 μL) and NaH (60% in mineral oil, 8.2 mg), and stirred for 19 h at ambient temperature. The reaction mixture was poured into H2O and extracted with EtOAc. The organic layer was collected and dried over Na2SO4 followed by solvent evaporation. Column chromatography (SiO2: hexane:EtOAc, from 9:1 to 1:1 v/v) yielded a fraction containing impure desired product 6-methoxymethoxy-5,7,8-trimethyl-2,3-dihydro-4H-thiochromen-4-one (<1 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was collected
  3. dry with materialdried over Na2SO4
  4. customfollowed by solvent evaporation
  5. customColumn chromatography (SiO2: hexane:EtOAc, from 9:1 to 1:1 v/v) yielded a fraction

Sources & evidence

ORD record
ord-49e07af7b85f412090ddcad2b0d33d18
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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