Potassium sodium tartarate → HCID 18782828, compound

HRID 1420789Notes

Reaction equation

HRID 1420789 reaction equation
[CH2:1]([CH:3]1[CH2:6][CH:5]([C:7](=[CH2:11])[C:8](=[O:10])[CH3:9])[C:4]1([CH3:13])[CH3:12])C.[C-:14]#[N:15].C([Al+]CC)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:8]([CH:7]1[CH:11]([C:14]#[N:15])[CH2:1][CH:3]2[CH2:6][CH:5]1[C:4]2([CH3:12])[CH3:13])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16686413Diethyl aluminum cyanideHCID 18782841HCID 18782841, compound

Product 1

HCID 18782828HCID 18782828, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

3-(3-Ethyl-2,2-dimethyl-cyclobutyl)-but-3-en-2-one (568 mg, 3.46 mmol) was dissolved in benzene (20 ml) under an atmosphere of dry N2. To the solution was added a 1.0 M solution of diethylaluminum cyanide (5.0 ml) in toluene. After stirring at ambient temperature for 30 minutes, a 10% aqueous solution of potassium sodium tartrate (20 ml) was added to the reaction. After stirring at ambient temperature for 30 minutes, the reaction was partitioned between CH2Cl2 and 0.1 N aqueous sodium hydroxide (NaOH). The CH2Cl2 layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give 551 mg of the titled compound as an oil: 1H NMR (CDCl3)δ 3.99 (dt, J=4.3, 11.0 Hz, 1H), 3.14 (dd, J=3.1, 4.6 Hz, 1H), 2.62 (m, 1H), 2.53 (m, 1H), 2.41 (m, 1H), 2.22 (m, 1H), 2.17 (s, 3H), 2.01 (m, 1H), 1.44 (d, J=10.6 Hz, 1H), 1.22 (s, 3H), 0.64 (s, 3H).

Workup

  1. stirringAfter stirring at ambient temperature for 30 minutes
  2. customthe reaction was partitioned between CH2Cl2 and 0.1 N aqueous sodium hydroxide (NaOH)
  3. washThe CH2Cl2 layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-05265fc2c4fa47e69c29adb730397aca
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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