Triethylamine → HCID 69705918, compound

HRID 392916Notes

Reaction equation

HRID 392916 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][C:16](=[O:32])[C:17]1[CH:22]=[C:21](I)[CH:20]=[CH:19][C:18]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35].[Al]>CN(C=O)C.C(OCC)(=O)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)I>[CH2:8]([O:15][C:16](=[O:32])[C:17]1[CH:22]=[C:21]([C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33])[CH:20]=[CH:19][C:18]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 5359268AluminumHCID 22934559HCID 22934559, compound

Product 1

HCID 69705918HCID 69705918, compoundYield 93.2%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pd(PPh3)2Cl2 (194 mg, 0.277 mmol), copper iodide (106 mg, 0.554 mmol) and triethylamine (0.8 mL, 5.44 mmol) were added to a solution of 2-benzyloxy-5-iodo-benzoic acid benzyl ester (1.23 g, 2.77 mmol) and trimethylsilyl acetylene (0.5 mL, 3.32 mmol) in anhydrous DMF (15 mL) at room temperature. The flask was covered with aluminum foil and stirred overnight. The mixture was diluted with ethyl acetate (50 mL) and washed with water (3×), 1N HCl (1×) and brine (1×), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (5% ethyl acetate/hexanes) to afford 1.07 g (93%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 1H, J=2 Hz); 7.52 (dd, 1H, J=9.1, 1 Hz); 7.38 (m, 10H); 6.95 (d, 1H, J=9.1 Hz); 5.31 (s, 2H); 5.17 (s, 2H); 0.1 (s, 9H).

Workup

  1. washwashed with water (3×), 1N HCl (1×) and brine (1×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2fd5755309ee4c25aec931d106778085
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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