tert-Butyl acetate → tert-Butyl 3-(2-(2-hydroxyethoxy)phenyl)-3-oxopropanoate

HRID 75552Notes

Reaction equation

HRID 75552 reaction equation
[C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])(=[O:3])[CH3:2].C(NC(C)C)(C)C.[Li].[O:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21](=[O:28])[O:20][CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>C1COCC1>[OH:20][CH2:19][CH2:18][O:17][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21](=[O:28])[CH2:2][C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]

Participants

6

Reactant 4

HCID 10908tert-Butyl acetateHCID 2113145H-1,4-Benzodioxepin-5-one, 2,3-dihydro-HCID 516892Sodium BicarbonateHCID 45051747Lithium diisopropylamine

Product 1

HCID 86684691tert-Butyl 3-(2-(2-hydroxyethoxy)phenyl)-3-oxopropanoateYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of tert-butyl acetate (7.96 g, 68.5 mmol) in anhydrous THF (100 mL) was added freshly prepared lithium diisopropyl amine (37 mL, 1.85 M in THF) dropwise over 15 min at −78° C., and the mixture was stirred at −78° C. for 30 min. 2H-benzo[e][1,4]dioxepin-5(3H)-one (10.2 g, 62.3 mmol) was added dropwise as a solution in THF (50 mL) at −78 C, and stirring was continued for 30 min. Saturated NaHCO3 solution was added and the mixture was extracted with EtOAc. The organic layer was dried (Na2SO4), and concentrated under reduced pressure to give the title compound (6.0 g, 77.9%) as a yellow oil, which was used directly in the next step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e8d88ce413740b385096770e8f0a27d
Source dataset
uspto-grants-2014_09
Patent number
US08835449B2

Reaction notes

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