Chloromethyl Methyl Ether → [3-(2-Hydroxy-ethyl)-benzyl]-[2-(2-methoxymethoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 553314Notes

Reaction equation

HRID 553314 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][OH:26])[CH:19]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:30][O:31][CH2:32]Cl>CN(C)C=O>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][OH:26])[CH:19]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:30][O:31][CH3:32])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 67165713[3-(2-Hydroxy-ethyl)-benzyl]-[2-(2-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67164978[3-(2-Hydroxy-ethyl)-benzyl]-[2-(2-methoxymethoxy-phenyl)-ethyl]-carbamic acid tert-butyl esterYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of [3-(2-hydroxy-ethyl)-benzyl]-[2-(2-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (123 mg) in anhydrous N,N-dimethylformamide (2 mL) was treated with sodium hydride (14 mg of 60% grade reagent) and the mixture stirred under nitrogen for 10 minutes. A solution of chloromethyl methyl ether (29 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 separated, dried and the solvent evaporated under reduced pressure to yield the sub-titled compound (110 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. customthe organic layer was separated
  4. customdried
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2f0c26107ed24d829f94484f07115771
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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