Methanol → HCID 19001663, compound

HRID 1195278Notes

Reaction equation

HRID 1195278 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:19](Br)=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([Li])CCC.CI.CO>CCOCC.CCCCCC.O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:19]([CH3:21])=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 19001633HCID 19001633, compoundHCID 178418339Butyllithium

Product 1

HCID 19001663HCID 19001663, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

3.0 g of 5-(2-benzyloxyethyl)-6-bromo-1,3-benzodioxole was dissolved in 100 m(of anhydrous ether. 8.5 ml of a 1.6 M solution of n-butyllithium in hexane was added to the solution at -78° C. and the reaction was conducted at -50° C. for 2 h. The reaction mixture was cooled again to -78° C. 6.4 g of methyl iodide was added thereto and the temperature was gradually elevated to room temperature. Methanol and water were added to the reaction mixture. After extraction with ethyl acetate, the extract was dried over magnesium sulfate and concentrated under reduced pressure to obtain a crude methyl compound. After purification according to silica gel column chromatography (ethyl acetate/ hexane=2:98), 1.9 g of the intended compound was obtained in the form of a pale yellow oil.

Workup

  1. customwas gradually elevated to room temperature
  2. extractionAfter extraction with ethyl acetate
  3. dry with materialthe extract was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a crude methyl compound
  6. customAfter purification

Sources & evidence

ORD record
ord-cff42e49f36945b790603d9208912868
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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