Triphenylphosphine → [2-(4-Tert-butoxyphenoxy)ethoxy](tert-butyl)dimethylsilane

HRID 513176Notes

Reaction equation

HRID 513176 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[O:13]([CH2:21][CH2:22]O)[Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:22][CH2:21][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2773621p-Tert-butoxyphenolHCID 5363146Diisopropyl azodicarboxylateHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

Product 1

HCID 86720567[2-(4-Tert-butoxyphenoxy)ethoxy](tert-butyl)dimethylsilaneYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Tert-butoxyphenol (1 g, 6.02 mmole), 2-(t-butyldimethylsiloxy)ethanol (1.38 g, 7.83 mmole), and PPh3 (2.05 g, 7.82 mmole) were combined in toluene (30 mL) at RT. To this was added DIAD (1.52 mL, 7.82 mmole) slowly at RT. After stirring overnight the mixture was concentrated. Flash column chromatography (Biotage-SNAP-50 g SiO2, 0-10% EtOAc/hexanes) gave the title compound (1.7 g, 87%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 6.90 (d, J=8.8 Hz, 2 H); 6.80 (d, J=8.8 Hz, 2 H); 4.03-3.92 (m, 4 H); 1.30 (s, 9 H); 0.91 (s, 9 H); 0.10 (s, 6H).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-798a77fb04ee4879875f0d3e02c9f746
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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