Hydrochloric Acid → methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

HRID 654987Notes

Reaction equation

HRID 654987 reaction equation
[CH3:1][C@@H:2]([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].C(N(C(C)C)CC)(C)C.[CH2:18]([O:25][CH2:26]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl.C(OCC)(=O)C>[CH2:18]([O:25][CH2:26][O:8][CH2:7][C@H:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Product 1

HCID 14348497methyl (S)-3-benzyloxymethyloxy-2-methylpropionate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl (S)-(+)-2-methyl-3-hydroxypropionate (2.0 g; 16.9 mmole) and diisopropylethylamine (2.2 g; 17.1 mmole) were dissolved in dry dichloromethane (2 ml), and benzyloxymethyl chloride (2.7 g; 17.3 mmole) was dropwise added thereto, followed by stirring for 1 hour. 1N Hydrochloric acid (10 ml) and ethyl acetate (20 ml) were added thereto, and the aqueous layer was extracted with ethyl acetate. The extract was combined with the organic layer, washed with a sodium bicarbonate solution and water and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography to give methyl (S)-3-benzyloxymethyloxy-2-methylpropionate.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washwashed with a sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a31efad7e8364d32bd45e1d90163e36e
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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