Dodecane → HCID 22492576, compound

HRID 2253523Notes

Reaction equation

HRID 2253523 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([SH:26])[CH:23]=[CH:24][CH:25]=1.CCCCCCCCCCCC>C(OCC)(=O)C.COCCOC>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([S:26][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 69258Methyl 3-iodobenzoateHCID 849893-Methoxybenzenethiol

Product 1

HCID 22492576HCID 22492576, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Cu(I) iodide (10 mg, 0.05 mmol), potassium carbonate (276 mg, 2.0 mmol) and Methyl 3-iodobenzoate (276 mg, 1.0 mmol) were charged into a screw-capped test tube with Teflon-lining. The tube was evacuated and backfilled with argon (3 cycles). Anhydrous DME (1.0 mL) and 3-methoxythiophenol (124 μL, 1.0 mmol) were added by syringes at room temperature. The tube was heated to 80° C. and stirred for 22 hours. The reaction mixture was then allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 μL, GC standard) were added. The aliquot was analyzed GC. The reaction mixture was then filtered and concentrated. The crude product was purified by column chromatography on silica gel using hexane/ethyl acetate=20/1 to afford colorless liquid as the titled product (220 mg, 81% yield). Rf=0.5 (hexane/ethyl acetate=10/1). 1H NMR (CDCl3, 300 MHz) δ 8.02-8.03 (m, 1 H), 7.89 (dt, 1 H, J=1.2 Hz, 8.1 Hz), 7.45-7.49 (m, 1 H), 7.34 (t, 1 H, J=7.5 Hz), 7.21 (t, 1 H, J=8.1 Hz), 6.86-6.92 (m, 2 H), 6.79 (ddd, 1 H, J=0.6 Hz, 2.4 Hz, 8.1 Hz), 4.34 (q, 2 H, J=7.2 Hz), 3.76 (s, 3 H), 1.37 (t, 3 H, J=7.2 Hz). 13C NMR (CDCl3, 75 MHz) δ 166.0, 160.2, 136.5, 136.3, 135.2, 132.0, 131.7, 130.3, 129.3, 128.4, 123.7, 116.6, 113.5, 61.5, 55.7, 14.7. IR (neat, cm−1) 3064, 2981, 2960, 2937, 2360, 2342, 1717. MS (EI) m/z (relative intensity) 288 (100), 243 (30). Anal. Cald. for C16H16O3S, Cald. C: 66.64, H: 5.59; Found C: 66.87, H: 5.66.

Workup

  1. customThe tube was evacuated
  2. customto reach room temperature
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e154b2af42b942469f997817edb10687
Source dataset
uspto-grants-2008_01
Patent number
US07323608B2

Reaction notes

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