Chloromethyl Methyl Ether → HCID 67253555, compound

HRID 536608Notes

Reaction equation

HRID 536608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:10][S:11][CH:12]=2)=[C:4]([O:20][CH3:21])[CH:3]=1.[H-].[Na+].Cl[CH2:25][O:26][CH3:27]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:25][O:26][CH3:27])=[CH:15][CH:14]=3)=[CH:10][S:11][CH:12]=2)=[C:4]([O:20][CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 67255854HCID 67255854, compound

Product 1

HCID 67253555HCID 67253555, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-(4-chloro-2-methoxyphenyl)thiophen-3-yl)phenol (700 mg, 2.1 mmol) in anhydrous THF (5 mL) was added NaH (90 mg, 2.3 mmol) at 0° C. After the mixture was stirred at the temperature for 0.5 h, chloro(methoxy) methane (184 mg, 2.3 mmol) was added. The mixture was stirred at 0° C. for 1 hour, and at room temperature for 2 hours. When TLC indicated the starting material was consumed, the mixture was quenched with water, and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to give the crude product, which was purified by column to give 3-(4-chloro-2-methoxyphenyl)-4-(4-(methoxymethoxy)phenyl)thiophene (720 mg, 90%) which was taken forward to Step 3.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hour
  2. waitat room temperature for 2 hours
  3. customwas consumed
  4. customthe mixture was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by column

Sources & evidence

ORD record
ord-d418390756dd4e06bf34789fcbf0108e
Source dataset
uspto-grants-2014_10
Patent number
US08859611B2

Reaction notes

Loading…