Chloromethyl Methyl Ether → HCID 17975839, compound

HRID 2108845Notes

Reaction equation

HRID 2108845 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[C:7](=[O:9])[CH:8]=1.C1[CH2:35][O:34][CH2:33]C1.[H-].[Na+].ClCOC>O>[CH3:33][O:34][CH2:35][O:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[C:7](=[O:9])[CH:8]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 10433304HCID 10433304, compound

Product 1

HCID 17975839HCID 17975839, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Hydroxymethyl-5-[5-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-pentyloxy]-4H-pyran-4-one EHT 5909 (0.10 g, 0.227 mmol) was charged in a 25 mL three necked round bottom flask equipped with a magnetic stirrer and under a nitrogen atmosphere. THF (6 mL) and NaH (60% dispersion in oil, 10 mg, 0.25 mmol) were added at room temperature. After the reaction mixture was stirred for 5 min, methyl choromethyl ether (18.1 μl, 0.24 mmol, 1.05 eq.) was added via syringe and the reaction mixture was stirred for 2 h 30 at room temperature. The reaction mixture was poured in H2O (60 mL) and extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by chromatography on silica using as eluent MeOH:CH2Cl2=2:98. After evaporation and drying to the vacuum pump a white pale yellow solid EHT 2168 was obtained (74 mg, 67% yield).

Workup

  1. customequipped with a magnetic stirrer and under a nitrogen atmosphere
  2. stirringthe reaction mixture was stirred for 2 h 30 at room temperature
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified by chromatography on silica using as eluent MeOH
  8. customAfter evaporation
  9. customdrying to the vacuum pump a white pale yellow solid EHT 2168
  10. customwas obtained (74 mg, 67% yield)

Sources & evidence

ORD record
ord-86f94aca3acb48b6ae184168a9f90dbb
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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