Sodium hydride → Methyl 2-[(4-iodobenzyl)oxy]-2-methylpropionate

HRID 505669Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].[I:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[I:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of sodium hydride (55% in liquid paraffin) (315 mg, 7.3 mmol) in THF (2 ml) was dropped a solution of methyl 2-hydroxyisobutyrate (0.84 g, 7.1 mmol) in THF (2 ml). The reaction mixture was stirred for 30 minutes at 60° C. Thereto was dropped a solution of 4-iodobenzyl bromide (2.0 g, 6.7 mmol) in THF (4 ml) at 60° C. The mixture was stirred for 5 hours at 60° C. Therein were added ethyl acetate and a saturated ammonium chloride solution. After stirring for 5 minutes the mixture was separated by a separating funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to give the subject compound (1.93 g, 86%).

Workup

stirringThe mixture was stirred for 5 hours at 60° C
stirringAfter stirring for 5 minutes the mixture
customwas separated by a separating funnel
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe solvent was removed in vacuo
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-5cf980b6dc3c4b92b2a91529ccfc73d5
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781479B2

Reaction notes

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