Iodine → HCID 90901709, compound

HRID 348246

Reaction equation

HRID 348246 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[I:6]I.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH2:18]([Si:20]([CH2:38][CH3:39])([CH2:36][CH3:37])[O:21][C@H:22]([C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][CH:30]=[CH:29]2)CC=O)[CH3:19]>[I-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1.CCOCC>[I:6][C:3](=[CH:2][CH2:1][C@@H:22]([C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[N:32]=[CH:31][CH:30]=[CH:29]2)[O:21][Si:20]([CH2:38][CH3:39])([CH2:36][CH3:37])[CH2:18][CH3:19])[CH3:4]

Participants

8

Reactant 4

HCID 807IodineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86586607HCID 86586607, compoundHCID 178418339Butyllithium

Product 1

HCID 90901709HCID 90901709, compound

Reagents, catalysts & solvents 3

HCID 78474Ethyltriphenylphosphonium iodideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A suspension of ethyltriphenylphosphonium iodide (7.9 μm) 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 μm) 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

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

Sources & evidence

ORD record
ord-23d1900e443444389920e9c6015c39e1
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Linked notes

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