Diethyl Ether → HCID 10443088, compound

HRID 1655954Notes

Reaction equation

HRID 1655954 reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[C:11]([Li])(C)(C)C.CN(C)[CH:18]=[O:19].[CH2:21]([O:23]CC)C>>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:1]([O:19][CH3:18])[O:10][CH3:11])[C:3]=1[CH:21]=[O:23]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 115693-MethoxybenzaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 10443088HCID 10443088, compound

Procedure

A solution of the dimethyl acetal of m-anisaldehyde (490 mg) in dry diethyl ether (10 mL) at 0° was treated with a 1.7 molar solution of t-butyllithium (1.75 mL). The solution was stirred for 1 h at 0°, followed by addition of anhydrous dimethylformamide (0.25 mL). The solution was allowed to warm to 23° over 15 h, quenched by the addition of water, and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by chromatography on silica using 90% hexane-ethyl acetate as eluent to afford the title compound as a pale yellow oil (255 mg).

Workup

  1. temperatureto warm to 23° over 15 h
  2. customquenched by the addition of water
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography on silica using 90% hexane-ethyl acetate as eluent

Sources & evidence

ORD record
ord-8c76dd86f9134b12b759d60e5cde3e17
Source dataset
uspto-grants-1993_10
Patent number
US05252560

Reaction notes

Loading…