Sodium Iodide → HCID 18443687, compound

HRID 459102Notes

Reaction equation

HRID 459102 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[I-].[Na+].[CH2:22](OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:23][C:24]#[CH:25]>C1(C)C=CC=CC=1.C(OCC)C>[CH2:25]([O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1)[CH2:24][C:23]#[CH:22]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 71034-HydroxybiphenylHCID 2720203-Butynyl p-toluenesulfonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18443687HCID 18443687, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-phenylphenol (0.774 g, 4.55 mmol) and potassium tert-butoxide (0.51 g, 4.55 mmol) in toluene (20 mL) was stirred for 1 h at room temperature. Sodium iodide (0.068 g, 0.45 mmol) and toluene-4-sulfonic acid but-3-ynyl ester (1.02 g, 4.55 mmol) were added, and the mixture heated to reflux for 24 hours. The mixture was cooled to room temperature, diluted with diethyl ether (20 mL), washed with water (2×20 mL). The organic layer was dried (MgSO4) and concentrated under vacuum. The residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.57) to give an oil (140 mg, 14%). 1H-NMR (200.15 MHz, CDCl3): δ 7.57–7.50 (m, 4H), 7.46–7.38 (m, 2H), 7.32 (d, 1H, J=7.3), 7.02–6.95 (m, 2H), 4.15 (t, 2H, J=7.0), 2.71 (dt, 2H, J=2.7, 7.3), 2.06 (t, 1H, J=2.7).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 24 hours
  3. washwashed with water (2×20 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 3:1, Rf0.57)

Sources & evidence

ORD record
ord-fe4194ec1bbe46e99200e9a05c80af39
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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