2-Trimethylsilyl-1,3-dithiane → HCID 17923977, compound

HRID 842606Notes

Reaction equation

HRID 842606 reaction equation
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[C:16]([C:18]1([C:25]2[C:30]3[N:31]=[C:32]([CH:34]([CH3:36])[CH3:35])[O:33][C:29]=3[C:28]([O:37][CH3:38])=[CH:27][CH:26]=2)[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)#[N:17]>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH:34]([C:32]1[O:33][C:29]2[C:28]([O:37][CH3:38])=[CH:27][CH:26]=[C:25]([C:18]3([C:16]#[N:17])[CH2:23][CH2:22][C:21](=[C:3]4[S:8][CH2:7][CH2:6][CH2:5][S:4]4)[CH2:20][CH2:19]3)[C:30]=2[N:31]=1)([CH3:36])[CH3:35]

Participants

7

Reactant 3

HCID 834132-Trimethylsilyl-1,3-dithianeHCID 97967974-Cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanone2×HCID 178418339Butyllithium

Product 1

HCID 17923977HCID 17923977, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

2-Trimethylsilyl-1,3-dithiane (2.1 ml, 11.01 mmol) is dissolved in absolute THF (56 ml) and cooled to −70° C. with stirring. A solution of n-butyllithium in n-hexane (6.9 ml, 11.1 mmol of a 1.6 molar solution) is then slowly added dropwise under a nitrogen atmosphere by means of a glass syringe and the mixture is stirred at −45° C. for a further 30 min. After cooling to −70° C. again, a solution of 4-cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanone (1.5 g, 4.80 mmol, compound 3) in absolute THE (33 ml) is slowly added dropwise. The mixture is stirred at −70° C. for 1 h and then slowly warmed to RT (about 2 h). For working-up, the reaction solution is diluted with ethyl acetate (80 ml) and extracted (2 times) with 0.1 N hydrochloric acid (80 ml). The organic phase is dried using magnesium sulfate, filtered off and concentrated in vacuo. Column chromatography affords the title compound (1.34 9) as a colorless solid. TLC, silica gel (glass plates), petroleum ether/ethyl acetate (85:15), Rf=0.6.

Workup

  1. stirringthe mixture is stirred at −45° C. for a further 30 min
  2. temperatureAfter cooling to −70° C. again
  3. stirringThe mixture is stirred at −70° C. for 1 h
  4. temperatureslowly warmed to RT (about 2 h)
  5. extractionextracted (2 times) with 0.1 N hydrochloric acid (80 ml)
  6. customThe organic phase is dried
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85693234786c40cdaaf8b42bf9062913
Source dataset
uspto-grants-2002_04
Patent number
US06376485B1

Reaction notes

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