4-Iodophenol → HCID 66956533, compound

HRID 2066671Notes

Reaction equation

HRID 2066671 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.I[CH2:10][C:11](=[CH2:21])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>>[C:17]([Si:14]([O:13][CH2:12][C:11]([CH2:21][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)=[CH2:10])([CH3:15])[CH3:16])([CH3:19])([CH3:20])[CH3:18]

Participants

4

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 11358863Tert-butyl(dimethyl)silyl 2-(iodomethyl)-2-propenyl ether

Product 1

HCID 66956533HCID 66956533, compoundYield 94%

Procedure

Alkylation of 4-iodophenol with iodide 165 (see Example 2GGG) and K2CO3 as in Example 2GGG above for 6 h, followed by chromatography of the product on silica gel, eluting with petroleum ether (foreruns) and then with 5% CH2Cl2/petroleum ether, gave tert-butyl({2-[(4-iodophenoxy)methyl]-2-propenyl}oxy)dimethylsilane (167) (94%) as an oil; 1H NMR (CDCl3) δ 7.54 (dt, J=8.9, 2.7 Hz, 2H), 6.70 (dt, J=8.9, 2.7 Hz, 2H), 5.25 (d, J=1.0 Hz, 1H), 5.19 (d, J=1.2 Hz, 1H), 4.51 (s, 2H), 4.23 (s, 2H), 0.91 (s, 9H), 0.07 (2 s, 6H); HRFABMS calcd for C16H26H26Si m/z [M+H]+ 405.0747. found 405.0739.

Workup

  1. customabove for 6 h
  2. washeluting with petroleum ether (foreruns)

Sources & evidence

ORD record
ord-00f1e016506a4e0e971b9fe8cfb13aa8
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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