Ethanol → HCID 86232698, compound

HRID 1161641Notes

Reaction equation

HRID 1161641 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].C[N:7]([CH:9]=O)[CH3:8].C[CH2:12][OH:13].OS([O-])(=O)=O.[Na+].[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>CCOCC.CC(=O)OCC>[CH3:22][O:23][C:24]1[CH:9]=[N:7][C:8]2[CH:5]=[CH:4][CH:3]=[C:2]([CH:12]=[O:13])[C:21]=2[CH:20]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 516919Sodium BisulfateHCID 178418339Butyllithium

Product 1

HCID 86232698HCID 86232698, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of intermediate A.ii (10 g) in THF (250 ml) cooled to −78° C., was added n-BuLi (22 ml). After 15 min, a solution of DMF (10 ml) in ether (20 ml) was quickly added. The solution was stirred 15 min and EtOH (5 ml), followed by 1M NaHSO4 (40 ml), was added. After warming to rt, the organic layer was diluted with EA (100 ml). The two layers were separated and the aq. layer was extracted once with EA (100 ml). The combined org. layers were washed with brine and concentrated to dryness. The residue was chromatographed (EA-Hex 1-2 then 1-1) to afford the title compound (4.75 g) as a yellowish solid.

Workup

  1. additionwas added
  2. customThe two layers were separated
  3. extractionthe aq. layer was extracted once with EA (100 ml)
  4. washlayers were washed with brine
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed (EA-Hex 1-2

Sources & evidence

ORD record
ord-766263dc9ce04f20a198b37a1e609fe2
Source dataset
uspto-grants-2010_10
Patent number
US07820655B2

Reaction notes

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