Triethylamine → tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate

HRID 64421Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][OH:10].[C:11]([O:15][C:16](=[O:19])[CH:17]=[CH2:18])([CH3:14])([CH3:13])[CH3:12].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C(OCC)(=O)C.O.CN(C=O)C>[OH:10][CH2:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1/[CH:18]=[CH:17]/[C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.64 g of (2-bromo-5-methylphenyl)methanol, 246 mg of bis(dibenzylideneacetone)palladium, 2.95 ml of tert-butylacrylate, 442 mg of tris(2-methylphenyl)phosphine, 2.5 ml of triethylamine, and 24 ml of DMF was stirred at 100° C. for 24 hours. After leaving to be cooled at room temperature, water and ethyl acetate were added thereto to carry out a layer separation operation. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.32 g of tert-butyl (2E)-3-[2-(hydroxymethyl)-4-methylphenyl]acrylate.

Workup

customAfter leaving
temperatureto be cooled at room temperature
customa layer separation operation
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-889565f5456a4cd5a1a167f7cafd3cb8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Reaction notes

Loading…