Thiophenol → HCID 66696608, compound

HRID 1672546Notes

Reaction equation

HRID 1672546 reaction equation
[C:1]([Si:5]([O:18][C@@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([O:29]C)[CH:23]=[CH:24][CH:25]=2)[CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>CN1CCOCC1.C(OCC)(=O)C.O>[Si:5]([O:18][C@H:19]1[CH2:20][C:21]2[C:22]([OH:29])=[CH:23][CH:24]=[CH:25][C:26]=2[CH2:27][CH2:28]1)([C:1]([CH3:3])([CH3:4])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 66696637HCID 66696637, compound

Product 1

HCID 66696608HCID 66696608, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 79724-MethylmorpholineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 26B (0.9 g, 2.2 mmol) in N-methylmorpholine (7 mL) was treated with potassium carbonate (0.3 g, 2.2 mmol) and thiophenol (0.23 mL, 2.24 mmol), and the mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate, and the combined organic extract was washed three times with water and once with brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel (5 to 20% ethyl acetate-hexane, eluant) to afford 0.45 g (52% yield) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 9.11 (br, 1H), 7.64 (m, 4H), 7.41 (m, 6H), 6.85 (t, J=7.6 Hz, 1H), 6.45-6.56 (m, 2H), 4.06 (m, 1H), 2.70-2.86 (m, 2H), 2.45-2.54 (m, 2H), 1.73 (m, 2H), 0.97 (s, 9H). MS (DCI+) m/z 403 (M+H)+, 420 (M+NH4)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. extractionthe combined organic extract
  5. washwas washed three times with water
  6. dry with materialonce with brine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel (5 to 20% ethyl acetate-hexane, eluant)

Sources & evidence

ORD record
ord-ed079df5422f478bb45f8cbe6ae289b2
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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