Water → HCID 18988278, compound

HRID 2396127Notes

Reaction equation

HRID 2396127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7]O.C(O[CH:17](OCC)[C:18]([O:20][CH2:21][CH3:22])=[O:19])C.FC(F)(F)[S:28](O[Si](C)(C)C)(=O)=O.O>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:28][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 65367Trimethylsilyl triflateHCID 80169Ethyl diethoxyacetateHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 18988278HCID 18988278, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part A. A solution of 3,4-dimethoxyphenethyl alcohol (4.63 g, 25.4 mmol), ethyl diethoxyacetate (5.00 mL, 28.0 mmol) and trimethylsilyl trifluoromethanesulfonate (0.50 mL, 2.58 mmol) in acetonitrile (50 mL) wasstirred at ambient temperature for 12 hours, then heated to reflux for 18 hours. The solution was cooled, and poured into water (200 mL). This was extracted with ethyl acetate (2×200 mL), and the extracts were washed with brine (200 mL), combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (1:9 ethyl acetate/hexane--1:4 ethyl acetate/hexane) to afford the product, ethyl 6,7-dimethoxy-1,2,3,4-tetrahydro-2-thianaphthalene-1-carboxylate, as an oil (1.68 g, 6.31 mmol, 25%). 1H NMR (CDCl3): δ 6.92 (1H,s); 6.62 (1H, s); 4.32-4.22 (3H, m); 4.04-3.96 (1H, m); 3.87 (3H, s); 3.86 (3H, s); 2.90-2.79 (2H, m); 1.32 (3H, t, J=7.0 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 269 (1%); 268 (7%); 267 (53%); 233 (5%); 193 (100%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. temperatureThe solution was cooled
  4. extractionThis was extracted with ethyl acetate (2×200 mL)
  5. washthe extracts were washed with brine (200 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residual oil was separated by flash chromatography (1:9 ethyl acetate/hexane--1:4 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-72579c992cb14dee9d9979110e08b3b5
Source dataset
uspto-grants-1996_02
Patent number
US05491152

Reaction notes

Loading…