Hydrochloric Acid → HCID 13075145, compound

HRID 602759Notes

Reaction equation

HRID 602759 reaction equation
[C:1]1([S:7]([CH2:10][C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(CCN(C)C)C.[Li]CCCC.[C:26]1(=[O:32])[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]1.Cl>COCCOC>[C:1]1([S:7]([CH:10]([CH:28]2[CH2:29][CH2:30][CH2:31][C:26](=[O:32])[CH2:27]2)[C:11]#[N:12])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 135942-Cyclohexen-1-oneHCID 82077PhenylsulphonylacetonitrileHCID 178418339Butyllithium

Product 1

HCID 13075145HCID 13075145, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To 9.4 g (0.052 mol) of benzenesulfonyl-acetonitrile in 200 mL of DME at −50° C., 7.8 mL (0.052 mol, 1 eq) of TMEDA and 32.4 mL (0.052 mL, 1 eq) of nBuLi (1.6M in hexane) were added and stirring was continued for 45 min. To the resulting white suspension, 4.98 g (0.052 mol, 1 eq) of cyclohex-2-enone were added and the temperature was raised to −10° C. within 4 hours. The reaction mixture was poured into 180 mL of 1M HCl, extracted with EtOAc, and the combined organic phases dried over Na2SO4. Evaporation of the solvent and recrystallisation from AcOEt/Et2O yielded 8.25 g (57%) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetonitrile as a racemic mixture of diastereomers, white crystals, MS: 278 (MH+) (in analogy to: E. Hatzigrigoriou, L. Wartski, Synth. Comm., 1983, 14(4), 319-235).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe combined organic phases dried over Na2SO4
  3. customEvaporation of the solvent and recrystallisation from AcOEt/Et2O

Sources & evidence

ORD record
ord-b49b1dc2f1814efc979509378c6b53b8
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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