Triphenylphosphine → 4-Chloro-2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(3-thienyl)butoxy]benzonitrile

HRID 352124Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][CH2:8][CH2:9][CH:10]([C:12]1[CH:16]=[CH:15][S:14][CH:13]=1)[OH:11])([CH3:4])[CH3:3].O[C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:28][C:26]1[CH:27]=[CH:20][C:21]([C:22]#[N:23])=[C:24]([O:11][CH:10]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH2:9][CH2:8][CH2:7][O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:17])[CH3:18])[CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The product from step (b) (1.164 g, 4.06 mmol) was dissolved in anhydrous tetrahydrofuran (80 ml) and 2-hydroxy-4-chlorobenzonitrile (624 mg, 4.06 mmol) and triphenylphosphine (1.172 g, 4.47 mmol) added. The solution was cooled to 0° C. and diethyl azodicarboxylate (0.71 ml, 4.47 mmol) added dropwise. The reaction was allowed to warm to room temperature and stirred for a further 18 h. The reaction was concentrated in vacuo and the residue chromatographed on flash silica, eluting with hexane:ethyl acetate (4:1), to afford the title compound as a colourless oil (1.12 g, 65%).

Workup

temperatureto warm to room temperature
concentrationThe reaction was concentrated in vacuo
customthe residue chromatographed on flash silica
washeluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record: ord-50f7048a69304facace18ee3dc7c4982
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743939B2

Reaction notes

Loading…