Lithium Hexamethyldisilazide → HCID 22730842, compound

HRID 2356131Notes

Reaction equation

HRID 2356131 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)=[C:15]([O:29][CH3:30])[CH:14]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:30][O:29][C:15]1[CH:14]=[C:13]([CH:11]=[CH2:1])[CH:18]=[CH:17][C:16]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 11558086Methyl 4'-formyl-2'-methoxy[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 22730842HCID 22730842, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of methyltriphenylphosphonium bromide (785 mg, 2.2 mmoL) in THF (5 mL) was treated with 1M lithium bis(trimethylsilyl) amide in THF (2.2 mL), stirred for 30 minutes, treated with a solution of Example 122I (540 mg, 2.0 mmol) in THF (2 mL), stirred for 1 hour, and filtered through a pad of silica gel (20 g). The pad was rinsed with 1:1 ether/dichlormethane and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% dichloromethane/hexanes to provide the desired product.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered through a pad of silica gel (20 g)
  3. washThe pad was rinsed with 1:1 ether/dichlormethane
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 20-50% dichloromethane/hexanes

Sources & evidence

ORD record
ord-20baf761bba846e5820c073f94b3fd83
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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