Triethylsilane → 3-(4-Benzyloxy-phenyl)-2,2-dimethyl-propionic acid ethyl ester

HRID 62885Notes

Reaction equation

HRID 62885 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH3:23])([CH3:22])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)O)[CH3:2].C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH3:23])([CH3:22])[CH2:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 461805233-(4-Benzyloxy-phenyl)-3-hydroxy-2,2-dimethyl-propionic acid ethyl ester

Product 1

HCID 461805243-(4-Benzyloxy-phenyl)-2,2-dimethyl-propionic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Benzyloxy-phenyl)-3-hydroxy-2,2-dimethyl-propionic acid ethyl ester (1.5 g, 4.57 mmol) obtained in Step B was dissolved in DCM (20 mL). Triethylsilane (0.81 mL, 5.03 mmol) was added thereto, and the reactant was cooled to 0˜5° C. After boron trifluoride diethylether (0.62 mL, 5.03 mmol) was added thereto at 0˜5° C., the mixture was heated to room temperature and stirred for 2 hours. Saturated sodium bicarbonate was added thereto, and the reactant was stirred. The separated organic layer was concentrated under reduced pressure, and the residue was purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (1.34 g, 94%).

Workup

  1. temperaturethe reactant was cooled to 0˜5° C
  2. stirringthe reactant was stirred
  3. concentrationThe separated organic layer was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-94606b290c6c43a6b53dee898eb0e226
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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