Acetaldehyde → HCID 67528997, compound

HRID 1159698Notes

Reaction equation

HRID 1159698 reaction equation
[CH2:1]([C@H:3]1[CH:8]=[CH:7][CH2:6][C@H:5]([CH3:9])[C@H:4]1[C:10](=[O:12])[CH3:11])[CH3:2].[CH3:13][CH2:14][O-].[Na+].[Li+].CC([N-]C(C)C)C.C(C)=O.CC1C=CC(S(O)(=O)=O)=CC=1.O>C(O)C.C1CCCCC1.O.C1COCC1>[CH2:1]([C@H:3]1[CH:8]=[CH:7][CH2:6][C@H:5]([CH3:9])[C@@H:4]1[C:10](=[O:12])/[CH:11]=[CH:13]/[CH3:14])[CH3:2]

Participants

10

Reactant 5

HCID 177AcetaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 2723922Sodium ethoxideHCID 2724682Lithium diisopropylamideHCID 67528778HCID 67528778, compound3×

Product 1

HCID 67528997HCID 67528997, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

A crude 80:20 mixture of 1-(rel-(1S,2S,6S)-/1-(rel-(1R,2S,6S)-2-ethyl-6-methylcyclohex-3-enyl)ethan-1-one (2.6 g) was prepared as described in Example 2 by EtONa catalyzed epimerization of 1-(rel-(1R,2S,6S)-2-ethyl-6-methylcyclohex-3-enyl)ethan-1-one (3.15 g, 18.9 mmol, Example 3) in ethanol (30 ml) at reflux (25 h). Aldolisation (LDA, AcH, THF) and water-elimination (PTSA.H2O, cyclohexane, reflux, 45 min.) gave a 83:17 mixture of 1-(rel-(1S,2S,6S)-/1-(rel-(1R,2S,6S)-2-ethyl-6-methylcyclohex-3-enyl)ethan-1-one (1.27 g, 2 steps: 42%).

Workup

  1. customwas prepared
  2. temperatureat reflux (25 h)
  3. customgave

Sources & evidence

ORD record
ord-19a03036a3614ca0bd92a6f5be0a3bad
Source dataset
uspto-grants-2010_10
Patent number
US07812195B2

Reaction notes

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