Ethyl Acetate → HCID 59138592, compound

HRID 1670726Notes

Reaction equation

HRID 1670726 reaction equation
C(O[CH:5]([C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.[CH3:19][O:20][C:21]([O:25][Si](C)(C)C)=[C:22]([CH3:24])[CH3:23].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:18][C:15]1[N:14]=[CH:13][C:12]([CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:22]([CH3:24])([CH3:23])[C:21]([O:20][CH3:19])=[O:25])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 59138690HCID 59138690, compound

Product 1

HCID 59138592HCID 59138592, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (6-chloropyridin-3-yl)(phenyl)methyl acetate (0.52 g, 2.0 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (2.0 mL, 9.8 mmol) in anhydrous dichloromethane (10 mL) was added titanium tetrachloride solution (1M in toluene, 4.4 mL, 4.4 mmol) dropwise at 0° C. under argon. After stirring at 0° C. for 48 hrs (refrigerator) and room temperature for 5 hours, the mixture was poured into a saturated aqueous sodium bicarbonate solution (40 mL) maintained at 0° C. The mixture was extracted with ethyl acetate (2×40 mL). The combined organic solutions were dried (Na2SO4) and concentrated. Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave methyl 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.48 g, 1.6 mmol, 80% yield) as a colorless liquid. MS found: (M+H)+=304.25.

Workup

  1. temperaturemaintained at 0° C
  2. extractionThe mixture was extracted with ethyl acetate (2×40 mL)
  3. dry with materialThe combined organic solutions were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9eaa3e224b1b457fb657ddcb75197077
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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