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

HRID 1056526Notes

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

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

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

Sources & evidence

ORD record: ord-8b742f04d61441beb899200d1ca726c1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399626B2

Reaction notes

Loading…