Imidazole → 1-(Tert-butyldimethylsilyloxy)-4-iodobut-2-yne

HRID 1714711Notes

Reaction equation

HRID 1714711 reaction equation
[Si:1]([O:8][CH2:9][C:10]#[C:11][CH2:12]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[I:19]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Si:1]([O:8][CH2:9][C:10]#[C:11][CH2:12][I:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 54618454-((Tert-butyldimethylsilyl)oxy)but-2-yn-1-ol

Product 1

HCID 111414181-(Tert-butyldimethylsilyloxy)-4-iodobut-2-yneYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(tert-Butyldimethylsilyloxy)-but-2-yn-4-ol (63, 4.0 g, 19.96 mmol), imidazole (1.80 g, 26.45 mmol), iodine (6.58 g, 25.95 mmol) and triphenylphosphine (6.80 g, 25.95 mmol) are treated in 100 ml dichloromethane according to J. Robertson et al. J. Chem. Soc., Perkin Trans. 1, 3389-3369, 2000. Work-up yields 4.42 g (71%) of a colourless oil. The product is used directly in the next step.

Sources & evidence

ORD record
ord-632d369607ef46129d6d7e30a88e646b
Source dataset
uspto-grants-2010_09
Patent number
US07799524B2

Reaction notes

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