Sodium hydride → Methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate

HRID 1051104Notes

Reaction equation

[H-].[Na+].[Si:3]([O:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CN(C)C=O>[Si:3]([O:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][CH2:19][C:20]([O:22][CH3:23])=[O:21])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydride (60% mineral oil dispersion, 0.35 g, 8.7 mmol) was added to a solution of 3-((t-butyldimethylsilyl)oxy)phenol (0.49 g, 2.2 mmol), methyl 2-bromoacetate (0.37 g, 2.4 mmol), and dimethylformamide (2 mL) in a 50 mL round bottom flask under a nitrogen atmosphere at room temperature. The solution was heated in a 50° C. oil bath and allowed to stir overnight for approximately 16 hours. The resulting mixture was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (200 mL). The organic extract was dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 0.5 g (77%) of methyl 2-(3-((t-butyldimethylsilyl)oxy)phenoxy)acetate.

Workup

temperatureThe resulting mixture was cooled to room temperature
customThe reaction was quenched with saturated aqueous ammonium chloride (100 mL)
extractionextracted with ethyl acetate (200 mL)
extractionThe organic extract
dry with materialwas dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record: ord-88e1e745a34e4e5fb8215360fe003fe8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388153B2

Reaction notes

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