Methyl Acrylate → Methyl 4-(2-t-butyldimethylsiloxyethyl)cinnamate

HRID 55318Notes

Reaction equation

[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].CN(C)CCN(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl>[O:1]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:20]=[CH:19][C:18]([O:22][CH3:23])=[O:21])=[CH:13][CH:12]=1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-(2-t-butyldimethylsiloxyethyl)bromobenzene (1.00 g), methyl acrylate (0.55 g), palladium(II) acetate (0.010 g), triphenylphosphine (0.017 g) and N,N,N',N'-tetramethylethylenediamine (0.48 ml) was heated at 140° C. for 24 hours under an atmosphere of argon. To the reaction mixture was added methylene chloride (30 ml), the formed insoluble materials were removed by filtration through a celite column, and the filtrate was concentrated under reduced pressure. To the residue was added diethyl ether (30 ml), and the formed insoluble materials were removed by filtration through a celite column. The filtrate was concentrated to dryness to give methyl 4-(2-t-butyldimethylsiloxyethyl)cinnamate (0.94 g) as a brown oily liquid.

Workup

customthe formed insoluble materials were removed by filtration through a celite column
concentrationthe filtrate was concentrated under reduced pressure
additionTo the residue was added diethyl ether (30 ml)
customthe formed insoluble materials were removed by filtration through a celite column
concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record: ord-e247632268cd47b280d1c37682a44f4b
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624948

Reaction notes

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