Iodine → HCID 67126114, compound

HRID 513994Notes

Reaction equation

HRID 513994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([CH3:19])(O)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[I:25]I>C(#N)C.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:19])[C:9]=2[I:25])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 67126101HCID 67126101, compound

Product 1

HCID 67126114HCID 67126114, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-2-methyl-1-phenylbut-3-yn-2-ol (3D) (1.77 g, 6.53 mmol) in acetonitrile (50 mL) was added sodium bicarbonate (1.097 g, 13.06 mmol), followed by iodine (4.974 g, 19.60 mmol). The reaction mixture was stirred for 1.5 h, then diluted with diethyl ether. The organic layer was washed with 1 M sodium thiosulfate solution (50 mL). The aqueous layer was back-extracted with diethyl ether and the combined organic layer was dried (MgSO4), filtered, concentrated, adsorbed onto silica gel and purified by flash column chromatography (silica gel, hexanes) to give 3E as an off-white solid (1.8733 g). 1H-NMR: 300 MHz, (CDCl3) δ 7.74 (d, J=6.6 Hz, 1H), 7.73 (s, 1H), 7.48-7.40 (m, 3H), 7.24-7.20 (m, 2H), 7.13 (d, J=8.1 Hz, 2H), 2.64 (s, 3 H).

Workup

  1. washThe organic layer was washed with 1 M sodium thiosulfate solution (50 mL)
  2. extractionThe aqueous layer was back-extracted with diethyl ether
  3. dry with materialthe combined organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, hexanes)

Sources & evidence

ORD record
ord-1aed4e397fe142d5a97373376bcb083a
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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