Tetrahydrofuran → HCID 59488823, compound

HRID 221944Notes

Reaction equation

HRID 221944 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:14][OH:15].[CH3:16][O:17][C:18]([CH3:20])=[CH2:19].[C:21](=[O:24])([O-])[O-].[K+].[K+].[CH2:27]1[CH2:31]OC[CH2:28]1>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:18]([CH3:20])([O:17][CH3:16])[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:14][O:15][C:27]([O:24][CH3:21])([CH3:31])[CH3:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 83002-MethoxypropeneHCID 11430Potassium CarbonateHCID 59279019HCID 59279019, compound

Product 1

HCID 59488823HCID 59488823, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst

Procedure

Under a nitrogen stream, to a solution of (2-bromo-4-hydroxymethyl-naphthalen-1-yl)-methanol (124 mg, 0.464 mmol) and pyridinium p-toluenesulfonate (3 mg, 0.012 mmol) in THF (5 mL) was added 2-methoxypropene (0.134 mL, 1.399 mmol) under ice cooling, and the resultant mixture was stirred at the same temperature for 1 hour. Saturated aqueous potassium carbonate was added thereto, and the resultant mixture was twice extracted with ethyl acetate. The organic layer was washed with saturated brine and dried (anhydrous magnesium sulfate). Solvent was then removed by distillation under reduced pressure, to thereby obtain the titled compound (191 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-86d4e4942a624de5bc06bdebf65b51ce
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

Loading…