Chloromethyl Methyl Ether → HCID 69054868, compound

HRID 2102987Notes

Reaction equation

HRID 2102987 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[S:8][CH2:7][CH2:6][C:5]2=[O:14].[CH3:16][O:17][CH2:18]Cl.[H-].[Na+]>C1COCC1>[CH3:16][O:17][CH2:18][O:1][C:2]1[C:3]([CH3:15])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[S:8][CH2:7][CH2:6][C:5]2=[O:14]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride2×HCID 69056590HCID 69056590, compound

Product 1

HCID 69054868HCID 69054868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-5,7,8-trimethyl-2,3-dihydro-4H-thiochromen-4-one (2.24 g) was dissolved in anhydrous THF (100 mL) and treated with chloromethyl methyl ether (0.918 mL) and NaH (60% in mineral oil, 483 mg). The resulting reaction mixture was stirred for 2 h turning bright yellow as NaH was added and then gradually becoming pale yellow. The reaction mixture was quenched with a small amount of H2O followed by solvent evaporation and preloading the residue onto SiO2. Column chromatography (SiO2: hexane:EtOAc, 95:5 v/v) yielded 6-methoxymethoxy-5,7,8-trimethyl-2,3-dihydro-4H-thiochromen4-one as a white solid (2.37 g).

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. customThe reaction mixture was quenched with a small amount of H2O
  4. customfollowed by solvent evaporation

Sources & evidence

ORD record
ord-13b49c89b119462db5f6a9335cc2ece2
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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