Acetic Acid → 4-Cyano-4-phenylmethyl-delta-valerolactone

HRID 2230534Notes

Reaction equation

HRID 2230534 reaction equation
[Si](OC[CH2:10][C:11]([CH2:21]C=C)([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]#[N:13])(C(C)(C)C)(C)C.ClCCl.[Mn]([O-])(=O)(=O)=O.[K+].S([O-])([O-])=O.[Na+].[Na+].[C:39]([OH:42])(=[O:41])[CH3:40]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[O-2].[O-2].[Mn+4].C(OCC)(=O)C.CCCCCC.O>[C:12]([C:11]1([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:21][O:42][C:39](=[O:41])[CH2:40][CH2:10]1)#[N:13]

Participants

10

Reactant 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 18464852HCID 18464852, compound

Product 1

HCID 184646504-Cyano-4-phenylmethyl-delta-valerolactone

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine 2-(2-(t-butyldimethylsilyloxy)ethyl)-2-allyl-3-phenylpropionitrile (1.19 g) and dichloromethane (25 mL) and water (25 mL). Add tetrabutyl ammonium bromide (0.01 g) and acetic acid (8.0 mL). Add potassium permanganate (2.24 g) portionwise over 2 hours. After 18 hours, add sodium sulfite to dissolve the precipitated manganese dioxide. Separate the layers and adjust the pH of the aqueous layer to about 2 using aqueous 1 M hydrochloric acid solution. Extract the aqueous layer three times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane to give 4-cyano-4-phenylmethyl-δ-valerolactone.

Workup

  1. customSeparate the layers
  2. extractionExtract the aqueous layer three times with dichloromethane
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-4a4bdfb8082042fba8b6843b2e319871
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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