Chloromethyl Methyl Ether → HCID 67166430, compound

HRID 553317Notes

Reaction equation

HRID 553317 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][OH:17])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29][O:30][CH2:31]Cl>CN(C)C=O>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][OH:17])[CH:10]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:29][O:30][CH3:31])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 67165990HCID 67165990, compound

Product 1

HCID 67166430HCID 67166430, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (2-hydroxy-benzyl)-[3-(2-hydroxy-ethyl)-benzyl]-carbamic acid tert-butyl ester (250 mg) in anhydrous N,N-dimethylformamide (2 mL) was treated with sodium hydride (29 mg of 60% grade reagent) and the mixture stirred under nitrogen for 10 minutes. A solution of chloromethyl methyl ether (62 mg) in anhydrous N,N-dimethylformamide (0.5 mL) was added dropwise followed by stirring at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous brine, the organic layer was washed twice with aqueous brine, separated, dried and the solvent evaporated under reduced pressure. The residue was purified on silica eluting with 30% ethyl acetate in isohexane to yield the sub-titled compound (145 mg).

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous brine
  3. washthe organic layer was washed twice with aqueous brine
  4. customseparated
  5. customdried
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified on silica eluting with 30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3e2344bf9e384ec9b30841342692cd40
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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