Water → HCID 86663285, compound

HRID 1038320Notes

Reaction equation

HRID 1038320 reaction equation
[OH:1][CH2:2][C:3]([CH2:10][OH:11])([CH2:8][OH:9])[C:4]([O:6][CH3:7])=[O:5].[CH2:12]([Si:14](Cl)([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].O>N1C=CC=CC=1>[CH2:12]([Si:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[O:11][CH2:10][C:3]([CH2:2][O:1][Si:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:12][CH3:13])([CH2:8][O:9][Si:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:12][CH3:13])[C:4]([O:6][CH3:7])=[O:5])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 13819ChlorotriethylsilaneHCID 86663284HCID 86663284, compound

Product 1

HCID 86663285HCID 86663285, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of methyl 3-hydroxy-2,2-bis(hydroxymethyl)propanoate (1 equivalent) in pyridine at rt is added triethylsilyl chloride (3-6 equivalents) and the mixture is stirred at temperatures between rt and 60° C. until the reaction is substantially complete as monitored by LCMS or TLC. Water is added and the mixture is extracted with diethyl ether. The combined extracts are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford methyl 3-(triethylsilyloxy)-2,2-bis((triethylsilyloxy)methyl)propanoate.

Workup

  1. extractionthe mixture is extracted with diethyl ether
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-6862a348884e4c0e97a7c90fe2deebc7
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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