Diethyl Ether → HCID 10465705, compound

HRID 1655955Notes

Reaction equation

HRID 1655955 reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][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:5]1[CH:6]=[CH:7][C:2]([CH:1]([O:19][CH3:18])[O:10][CH3:11])=[C:3]([CH:4]=1)[CH:21]=[O:23]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 312444-MethoxybenzaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 10465705HCID 10465705, compound

Procedure

A solution of the dimethyl acetal of p-anisaldehyde (5.3 g) in dry diethyl ether (90 mL) at 0° was treated with a 1.7 molar solution of t-butyl lithium (20.5 mL). The solution was stirred for 1.5 h at 0°, followed by addition of anhydrous dimethylformamide (2.9 mL). The solution was allowed to warm to 23° over 1 h, quenched by the addition of water, and extracted with ethyl acetate (2×200 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 (2.63 g).

Workup

  1. temperatureto warm to 23° over 1 h
  2. customquenched by the addition of water
  3. extractionextracted with ethyl acetate (2×200 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-249ffdfeb4ea41dbb24ccc45315852fc
Source dataset
uspto-grants-1993_10
Patent number
US05252560

Reaction notes

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