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

HRID 2247836Notes

Reaction equation

HRID 2247836 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)methanol3×

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 (Compound 25, 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. customat 0°
  2. washthe reaction mixture was washed successively with water, dilute hydrochloric acid and water
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate) dichloromethane layer
  5. customgave an oil, which
  6. customwas purified by preparative silica TLC (developed with 30% ethyl ether/hexane)
  7. customto give the title ether as a colorless oil

Sources & evidence

ORD record
ord-4c6252ea225e406fbbe81de3b88e4d13
Source dataset
uspto-grants-1991_08
Patent number
US05037811

Reaction notes

Loading…