2-Methoxypropene → HCID 69280805, compound

HRID 1396301Notes

Reaction equation

HRID 1396301 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[O:19][C@H:18]2[C@H:14]([N:15]=[C:16]([N:20]([CH3:22])[CH3:21])[S:17]2)[C@@H:13]([OH:23])[C@@H:12]1[OH:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH3:26][C:27]1C=CC(S(O)(=O)=O)=C[CH:28]=1.COC(C)=C>CN(C=O)C>[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:12]2[C@H:13]([O:23][C:27]([CH3:28])([CH3:26])[O:24]2)[C@@H:14]2[C@@H:18]([S:17][C:16]([N:20]([CH3:21])[CH3:22])=[N:15]2)[O:19]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 83002-MethoxypropeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 69083776HCID 69083776, compound

Product 1

HCID 69280805HCID 69280805, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 154 (3.0 g, 8.5 mmol) in DMF (20 mL) was added 4-methylbenzenesulfonic acid hydrate (3.2 g, 17 mmol) and 2-methoxyprop-1-ene (6.1 g, 85 mmol) sequentially. The resulting solution was stirred for 15 minutes at room temperature, before the reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (20 mL), which was then extracted with dichloromethane (3×20 mL). The combined organic layer was washed with brine (2×10 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The crude residue was purified by flash column chromatography with 1%-10% ethyl acetate in petroleum ether to afford 155 as an off-white solid (1.6 g, 48%). (ES, m/z): [M+H]+ 393.0; 1H NMR (300 MHz, CDCl3) δ 8.08-8.05 (m, 2H), 7.63-7.45 (m, 3H), 6.32-6.30 (m, 1H), 4.60-4.52 (m, 2H), 4.41-4.31 (m, 2H), 3.97-3.91 (m, 1H), 3.70-3.63 (m, 1H), 3.55-3.50 (m, 1H), 3.39-3.30 (m, 1H), 3.10 (s, 6H), 1.50 (s, 6H).

Workup

  1. customwas quenched by the addition of saturated aqueous sodium bicarbonate solution (20 mL), which
  2. extractionwas then extracted with dichloromethane (3×20 mL)
  3. washThe combined organic layer was washed with brine (2×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was purified by flash column chromatography with 1%-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-a89aa5623efe4ae49ae5a2b5fa8ecd76
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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