Water → HCID 54281692, compound

HRID 581008Notes

Reaction equation

HRID 581008 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]([C:12]1([O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:17]2[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]2)[CH2:13]1)#[CH:11].O>CN(C)C=O.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:11]#[C:10][C:12]1([O:20][Si:21]([CH3:23])([CH3:22])[CH3:24])[CH:17]2[CH2:16][CH2:15][N:14]([CH2:19][CH2:18]2)[CH2:13]1)=[O:5]

Participants

8

Reactant 3

HCID 962WaterHCID 811292-BromobenzaldehydeHCID 53957647HCID 53957647, compound

Product 1

HCID 54281692HCID 54281692, compoundYield 64.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Bis(triphenylphosphine)-palladium(II) chloride (175 mg) and copper(I) iodide (85 mg) were added to a solution of 2-bromobenzaldehyde (2.03 g) and 3-ethynyl-3-trimethylsilyloxyquinuclidine (2.23 g) in dimethyl formamide (25 ml) and triethylamine (5 ml) at ambient temperature under an atmosphere of argon. The reaction mixture was stirred at ambient temperature for 21 hours. The reaction mixture was poured into water (150 ml) and extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were combined, filtered, washed with water (2×100 ml), brine (100 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography on alumina (Alumina N 32-63) using a 40:60 (v/v) mixture of ethyl acetate and isohexane as eluent to give 3-[2-{2-formylphenyl}ethynyl]-3-trimethylsilyloxyquinuclidine as an oil (2.1 g), NMR: 0.00 (9H, s), 1.1-1.3 (1H, m), 1.35-1.54 (1H, m), 1.82-1.90 (1H, m), 2.5 (4H, t), 2.73 (1H, d), 3.07 (1H,d), 7.38-7.48 (2H, m), 7.5-7.6 (1H, m), 7.68-7.75 (1H, m), 10.2 (1H, s), m/z 328 (M+H).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. filtrationfiltered
  3. washwashed with water (2×100 ml), brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on alumina (Alumina N 32-63)
  7. additiona 40:60 (v/v) mixture of ethyl acetate and isohexane as eluent

Sources & evidence

ORD record
ord-8a33f549670c457d964216195d92411b
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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