Iodine → (6S)-3-iodo-6-(6-quinolyl)-6-(triethylsilyloxy)-3-hexene

HRID 2181754Notes

Reaction equation

[I-:1].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].C([Li])CCC.II.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH2:41]([Si:43]([CH2:61][CH3:62])([CH2:59][CH3:60])[O:44][C@H:45]([C:49]1[CH:50]=[C:51]2[C:56](=[CH:57][CH:58]=1)[N:55]=[CH:54][CH:53]=[CH:52]2)[CH2:46][CH:47]=O)[CH3:42]>O1CCCC1.CCOCC>[I:1][C:2](=[CH:47][CH2:46][C@@H:45]([C:49]1[CH:50]=[C:51]2[C:56](=[CH:57][CH:58]=1)[N:55]=[CH:54][CH:53]=[CH:52]2)[O:44][Si:43]([CH2:61][CH3:62])([CH2:59][CH3:60])[CH2:41][CH3:42])[CH2:3][CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

A suspension of propyltriphenylphosphonium iodide (8.2 gm) in 150 mL of tetrahydrofuran is treated with a 2.5 M solution of n-butyllithium (7.17 mL) at ambient temperature. The resulting red solution is transferred via cannula into a vigorously stirred solution of iodine (4.54 gm) in 150 mL of tetrahydrofuran cooled to −78° C. The resulting suspension is stirred for 5 minutes, then gradually warmed to −30° C. A 1.0 M solution of sodium hexamethyldisilazide (17.3 mL) is then added dropwise to form a red solution. A solution of (3S)-3-(triethylsilyloxy)-3-(6-quinolyl)propanal (1.9 gm) in 10 mL of tetrahydrofuran is then added dropwise, and stirring is continued at −30° C. for 30 minutes. The mixture is diluted with ether, filtered through a pad of Celite, and concentrated. The product is purified by flash chromatography on silica gel.

Workup

temperaturegradually warmed to −30° C
customto form a red solution
stirringstirring
waitis continued at −30° C. for 30 minutes
filtrationfiltered through a pad of Celite
concentrationconcentrated
customThe product is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-9a572146f6c349df8fa5ca8bbd67a359
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06893859B2

Reaction notes

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