Acetone Cyanohydrin → 3-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]propionitrile

HRID 2223869Notes

Reaction equation

HRID 2223869 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28]O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)(O)[C:32]#[N:33].C(P(CCCC)CCCC)CCC>C1C=CC=CC=1>[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][C:32]#[N:33])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:18])([CH3:16])[CH3:17])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 13831TributylphosphineHCID 574278602-[1-(2-tert-Butyldiphenylsiloxyethyl)cyclohexyl]ethanol

Product 1

HCID 597149653-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]propionitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of [2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethanol (1.25 g) dissolved in benzene (15 mL) were added acetone cyanohydrin (0.40 mL), tri-n-butylphosphine (1.08 mL) and 1,1-azobis(N,N-dimethylformamide) (754 mg). The solution was stirred at room temperature for 18 hours. The solvent was distilled off under reduced pressure, ethyl acetate was added and insolubles were filtered off. The solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=5:1) to give the title compound (1.07 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  2. additionwas added
  3. filtrationinsolubles were filtered off
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-d79357db47624000924f6636a0f5f3b9
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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