Phenylacetylene → HCID 22042608, compound

HRID 1791007Notes

Reaction equation

HRID 1791007 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH3:14][N:15]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1)[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C1COCC1>[OH:36][C:31]([C:28]1[CH:27]=[CH:26][C:25]([N:15]([CH3:14])[S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])=[CH:30][CH:29]=1)([C:32]([F:33])([F:34])[F:35])[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 22042580HCID 22042580, compoundHCID 178418339Butyllithium

Product 1

HCID 22042608HCID 22042608, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.18 g of phenylacetylene (1.75 mmol) in 5 mL of THF was added dropwise 0.76 mL of n-BuLi (2.5M in hexane) at −78° C. The color of the solution turned dark blue and the mixture was stirred at −78° C. for 30 min. Then 0.5 g of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A) in 5 ml of THF was added and the resultant mixture stirred at −78° C. for 2 h. After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 7:3) to give the title compound. 1H NMR (CDCl3) δ 3.19 (s, 3H), 3.26 (br s, 1H), 7.17 (d, J=8.7 Hz, 2H), 7.34–7.60 (m, 10H), 7.74 (d, J=8.7 Hz, 2H). Mass Spectrum (CI+) m/e=446.0 (M+1).

Workup

  1. customAfter this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 7:3)

Sources & evidence

ORD record
ord-272692371c074155b8e4bdc7870a2a38
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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