Ethyl Acetate → 1-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

HRID 1602402Notes

Reaction equation

HRID 1602402 reaction equation
C(P(=O)(OCC)[O:4][CH2:5]C)#N.[H-].[Na+].[F:13][C:14]1[C:22]([CH:23]=O)=[C:18]2[CH:19]=[CH:20][O:21][C:17]2=[CH:16][CH:15]=1.[C:25](OCC)(=[O:27])C>O1CCCC1.[Cl-].[Na+].O>[CH3:5][O:4][CH:19]([O:27][CH3:25])[CH2:20][O:21][C:17]1[CH:16]=[CH:15][C:14]([F:13])=[C:22]([CH3:23])[CH:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 76257Diethyl cyanophosphonateHCID 196116515-Fluorobenzofuran-4-carbaldehyde

Product 1

HCID 196116591-(2,2-Dimethoxyethoxy)-4-fluoro-3-methylbenzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of diethyl cyanophosphonate (2.79 g) in dry tetrahydrofuran (10 ml) was added to a suspension of sodium hydride (60% oil dispersion; 0.63 g) in THF (16 ml) over 5 mins with ice cooling. After 15 min, a solution of 5-fluorobenzofuran-4-carbaldehyde (2.15 g) in THF (10 ml) was added and after 5 mins the solution was warmed up and stirred at room temperature for 3 h. Brine (20 ml) and ethyl acetate (20 ml) were added, the phases separated and the aqueous extracted with ethyl acetate (2×25 ml). The extracts were dried and evaporated and the residue purified by chromatography (Biotage Flash 40; 90 g; ethyl acetate:hexane 1:9) to give the title compound as a cream solid (1.97 g)

Workup

  1. temperaturewas warmed up
  2. customthe phases separated
  3. extractionthe aqueous extracted with ethyl acetate (2×25 ml)
  4. customThe extracts were dried
  5. customevaporated
  6. customthe residue purified by chromatography (Biotage Flash 40; 90 g; ethyl acetate:hexane 1:9)

Sources & evidence

ORD record
ord-b312c656aa4a4121b93879e8f2d7bb95
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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