2-Methoxypropene → HCID 59488769, compound

HRID 221947Notes

Reaction equation

HRID 221947 reaction equation
[Br:1][C:2]1[C:3]([CH2:21][OH:22])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)[CH:8]=[CH:7][CH:6]=2.[CH3:23][O:24][C:25]([CH3:27])=[CH2:26].C(=O)([O-])O.[Na+]>C1COCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=2)=[CH:4][C:3]=1[CH2:21][O:22][C:25]([O:24][CH3:23])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 59488774HCID 59488774, compound

Product 1

HCID 59488769HCID 59488769, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, to a solution of [3-bromo-5-[(4-ethylphenyl)methyl]-naphthalen-2-yl]-methanol (326.2 mg, 0.92 mmol) and pyridinium p-toluenesulfonate (4.6 mg, 0.02 mmol) in THF (3.0 mL) was added 2-methoxypropene (0.44 mL, 4.6 mmol) under ice-cooling, and the resultant mixture was stirred at the same temperature for 1.5 hours. Saturated aqueous sodium hydrogen carbonate was added thereto. The resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, to thereby obtain the titled compound (393.2 mg, 100%).

Workup

  1. temperaturecooling
  2. extractionThe resultant mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dac3bd636f5546449ef33bf3b694aa94
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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