N,N-Dimethylaniline → 4-(Methoxyethoxymethoxymethyl)-2-trimethylsilylfuran

HRID 1090881Notes

Reaction equation

HRID 1090881 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([Si:15]([CH3:18])([CH3:17])[CH3:16])[O:13][CH:14]=1.CN(C)C1C=CC=CC=1>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:8][CH2:9][C:10]1[CH:11]=[C:12]([Si:15]([CH3:18])([CH3:17])[CH3:16])[O:13][CH:14]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 13333558(2-Trimethylsilyl-4-furyl)methanol2×

Product 1

HCID 150370374-(Methoxyethoxymethoxymethyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyethoxymethyl chloride (0.11 ml, 0.96 mmol) was added to a solution of 4-hydroxymethyl-2-trimethylsilylfuran, also known as (2-trimethylsilyl-4-furyl)methanol, (162.8 mg, 0.96 mmol) and dimethylaniline (0.13 ml, 0.1 mmol) in dichloromethane (5 ml) at 0°. After stirring at room temperature overnight (ca. 16 hours), the reaction mixture was washed successively with water, dilute hydrochloric acid and water. Evaporation of the dried (magnesium sulfate) dichloromethane layer gave an oil, which was purified by preparative silica TLC (developed with 30% ethyl ether/hexane) to give the title ether as a colorless oil.

Workup

  1. washthe reaction mixture was washed successively with water, dilute hydrochloric acid and water
  2. customEvaporation of the
  3. dry with materialdried (magnesium sulfate) dichloromethane layer
  4. customgave an oil, which
  5. customwas purified by preparative silica TLC (developed with 30% ethyl ether/hexane)
  6. customto give the title ether as a colorless oil

Sources & evidence

ORD record
ord-cafef7f61f4b4529b7f24c4cc231984f
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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