Hydrochloric Acid → HCID 333809, compound

HRID 1919240Notes

Reaction equation

HRID 1919240 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br-].[CH2:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:38]([C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH:44]=O)([OH:40])=[O:39].Cl>C1COCC1.C(OCC)(=O)C>[C:13]1([CH:12]=[CH:44][C:43]2[CH:42]=[C:41]([CH:48]=[CH:47][CH:46]=2)[C:38]([OH:40])=[O:39])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120773-CarboxybenzaldehydeHCID 2733832Lithium Hexamethyldisilazide2×HCID 2734970Benzyltriphenylphosphonium bromide

Product 1

HCID 333809HCID 333809, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 M solution of lithium bis(trimethylsilyl) amide (3.3 mL, 3.3 mmol) in THF was added to a stirred suspension of benzyltriphenylphosphonium bromide (1.44 g, 3.6 mmol) in THF (35 mL) at 0° C. The resulting orange solution was added via cannula to a mixture of 3-carboxybenzaldehyde (500 mg, 3.3 mmol) and lithium bis(trimethylsilyl)amide (3.3 mL, 3.3 mmol) in THF (10 mL). The mixture was stirred overnight at room temperature. A 1N solution of HCl (75 mL) and ethyl acetate (75 mL) were added and the separated aqueous layer was extracted with ethyl acetate (3×50 mL), dried (MgSO4 anh.) filtered and evaporated. The residue was purified by HPLC (10:95 CH3CN:H2O, TFA 0.1%) to afford 130 mg of the title compound (17%).

Workup

  1. extractionthe separated aqueous layer was extracted with ethyl acetate (3×50 mL)
  2. dry with materialdried (MgSO4 anh.)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by HPLC (10:95 CH3CN:H2O, TFA 0.1%)

Sources & evidence

ORD record
ord-f1ad1fc3e74643799d24f0bcdfe0d3aa
Source dataset
uspto-grants-2012_05
Patent number
USRE043343E1

Reaction notes

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