Acetaldehyde → HCID 53995682, compound

HRID 2417654Notes

Reaction equation

HRID 2417654 reaction equation
[CH3:1][N:2]([CH3:26])[N:3]=[C:4]([CH:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)[CH3:7])[CH3:5].C([N-]C(C)C)(C)C.[Li+].[CH:35](=[O:37])[CH3:36].O.C(Cl)Cl>C1COCC1>[CH3:26][N:2]([CH3:1])[N:3]=[C:4]([CH2:5][CH:35]([OH:37])[CH3:36])[CH:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)[CH3:7]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 2724682Lithium diisopropylamideHCID 21908982Water methylene chlorideHCID 54005021HCID 54005021, compound

Product 1

HCID 53995682HCID 53995682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[4-(4-trifluoromethylphenoxy)phenoxy]-2-butanone N,N-dimethylhydrazone (5.4 mmol) in THF (15 ml) under nitrogen is added lithium diisopropylamide (6.6 mmol) in THF (15 ml) at 0° for 4 hours. The resulting solution is cooled to -78°, and to it is added ethanal (6.6 mmol). After 1 hour at -78°, the reaction mixture is allowed to warm to 0° and is poured into water/methylene chloride (3:1). The organic phase is separated (3X), and the combined organic extracts are dried over sodium sulfate and concentrated to give 5-hydroxy-2-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hexanone N,N-dimethylhydrazone (cpd. 25, Table C).

Workup

  1. temperatureThe resulting solution is cooled to -78°
  2. temperatureto warm to 0°
  3. customThe organic phase is separated (3X)
  4. dry with materialthe combined organic extracts are dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-752d70d855aa41b6a1a1ceeea9c871b9
Source dataset
uspto-grants-1984_09
Patent number
US04469872

Reaction notes

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