Imidazole → Tert-butyl {3-iodo-2-[(4-iodophenoxy)methyl]propoxy}dimethylsilane

HRID 2066673Notes

Reaction equation

HRID 2066673 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1)[CH2:11]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I:22]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1>>[C:4]([Si:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1)[CH2:11][I:22])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 669567553-{[Tert-butyl(dimethyl)silyl]oxy}-2-[(4-iodophenoxy)methyl]-1-propanol

Product 1

HCID 66955564Tert-butyl {3-iodo-2-[(4-iodophenoxy)methyl]propoxy}dimethylsilaneYield 94%

Procedure

Iodination of alcohol 169 with I2, PPh3 and imidazole as in Example 2GGG above for 12 h, followed by chromatography of the product on silica gel, eluting with 0-5% CH2Cl2/petroleum ether (foreruns) and then with 5-10% CH2Cl2/petroleum ether, gave tert-butyl {3-iodo-2-[(4-iodophenoxy)methyl]propoxy}dimethylsilane (171) (94%) as a colourless oil; 1H NMR (CDCl3) δ 7.55 (dt, J=9.0, 2.7 Hz, 2H), 6.68 (dt, J=9.0, 2.7 Hz, 2H), 3.98 (dd, J=9.4, 5.7 Hz, 1H), 3.92 (dd, J=9.4, 6.2 Hz, 1H), 3.74 (dd, J=10.1, 5.6 Hz, 1H), 3.69 (dd, J=10.1, 5.6 Hz, 1H), 3.38 (dd, J=10.0, 5.9 Hz, 1H), 3.35 (dd, J=10.0, 6.1 Hz, 1H), 2.09 (sept, J=5.8 Hz, 1H), 0.89 (s, 9H), 0.06 (2 s, 6H); HRFABMS calcd for C16H27I2O2Si m/z [M+H]+ 532.9870. found 532 9864.

Workup

  1. customabove for 12 h
  2. washeluting with 0-5% CH2Cl2/petroleum ether (foreruns)

Sources & evidence

ORD record
ord-fb9e322487644326a0913aaf0c6a152a
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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