Ethyl Acetate → HCID 57658011, compound

HRID 1670818Notes

Reaction equation

HRID 1670818 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH3:2].[CH:31]([N-:34]C(C)C)(C)[CH3:32].[Li+].BrCC#N.C(OCC)(=O)C>C1COCC1>[CH2:1]([O:3][C:4](=[O:30])[CH:5]([CH:6]1[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:32][C:31]#[N:34])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11534BromoacetonitrileHCID 2724682Lithium diisopropylamideHCID 57658015HCID 57658015, compound

Product 1

HCID 57658011HCID 57658011, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Treat a −78° C. solution of [4-(tert-butyl-diphenyl-silanyloxy)-cyclohexyl]-acetic acid ethyl ester (4.71 g, 11.49 mmol) in THF (40 mL) with a 1.6M solution of lithium diisopropylamide in THF (7.18 mL, 14.36 mmol) and stir at −78° C. for 20 minutes under N2. Treat the reaction with bromoacetonitrile (1.71 g, 14.36 mol) and stir at −78° C. for 2 hours. Warm the reaction to room temperature and stir for 2 hours. Quench the reaction with 1N HCl at 0° C. Dilute the reaction with ethyl acetate and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 25% to 40% ethyl acetate in hexanes gradient to afford 2.62 g (50%) of the titled product. MS (m/z): 450 (M+1).

Workup

  1. additionTreat
  2. stirringstir at −78° C. for 2 hours
  3. temperatureWarm
  4. customthe reaction to room temperature
  5. stirringstir for 2 hours
  6. customQuench
  7. customthe reaction with 1N HCl at 0° C
  8. additionDilute
  9. washwash with water
  10. dry with materialDry the organic layer (Na2SO4)
  11. customremove the solvent in vacuo
  12. customto afford crude product
  13. custompurify with a 25% to 40% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-3c23931526f64177b30995d82f59d6a3
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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