Triethylsilane → Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester

HRID 1046443Notes

Reaction equation

HRID 1046443 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][Si](C)(C)C.[O:14]1[CH2:18][CH2:17][C:16](=O)[CH2:15]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][CH:16]1[CH2:17][CH2:18][O:14][CH2:15]1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 5293923-OxotetrahydrofuranHCID 866501662,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester

Product 1

HCID 58114071Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl esterYield 89.5%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

2,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester (478 mg, 2.34 mmol) was added to a solution of dihydro-furan-3-one (168 mg, 1.95 mmol) and FeCl3 (16 mg, 0.097 mmol) in nitromethane (6.0 mL) at 0° C. Triethylsilane (0.374 mL, 2.33 mmol) was added and the reaction was warmed to room temperature and stirred for 2 h. Sat. NaHCO3 was added and the reaction was extracted with dichloromethane. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to give a pale liquid. Purification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes provided dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester (353 mg, 75%) as a colorless liquid.

Workup

  1. extractionthe reaction was extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a pale liquid
  7. customPurification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6d5022cbbad94e489dcc14d88265b5b8
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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