2-Methoxypropene → 3-[2-(1-Methoxy-1-methyl-ethoxy)-ethyl]-7-(1-methoxy-1-methyl-ethoxymethyl)-benzo[b]thiophene

HRID 221933Notes

Reaction equation

HRID 221933 reaction equation
[OH:1][CH2:2][C:3]1[C:8]2[S:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:15][O:16][C:17]([CH3:19])=[CH2:18].[C:20]1([CH3:30])C=CC(S(O)(=O)=O)=C[CH:21]=1.[NH+]1C=CC=CC=1.[C:37](=O)([O-])[OH:38].[Na+]>C1COCC1>[CH3:15][O:16][C:17]([CH3:19])([O:14][CH2:13][CH2:12][C:11]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][O:1][C:20]([O:38][CH3:37])([CH3:30])[CH3:21])[C:8]=2[S:9][CH:10]=1)[CH3:18]

Participants

6

Reactant 4

HCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 22033616Pyridinium.p-toluenesulfonateHCID 594887992-(7-Hydroxymethyl-benzo[b]thiophen-3-yl)-ethanol

Product 1

HCID 594888273-[2-(1-Methoxy-1-methyl-ethoxy)-ethyl]-7-(1-methoxy-1-methyl-ethoxymethyl)-benzo[b]thiopheneYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, to a solution (3 mL) of 2-(7-hydroxymethyl-benzo[b]thiophen-3-yl)-ethanol (78 mg, 0.37 mmol) in THF were added 2-methoxypropene (358 μL, 3.7 mmol) and pyridinium p-toluenesulfonic acid (1 mg, 0.037 mmol) at 0° C. The resultant solution was stirred at the same temperature for 30 minutes, and then saturated aqueous sodium hydrogen carbonate was added thereto. The resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. Solvent was then removed by distillation under reduced pressure, to thereby obtain a crude product of the titled compound (123 mg, 94%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customSolvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a0c93d37e58b4a259d7abf57572ab63c
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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