Ethyl Acetate → Methyl 3-cyano-4-methylbenzoate

HRID 2071100

반응식

HRID 2071100 반응식
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=O.[NH4+:13].[OH-:14].[CH3:15]COC(C)=O>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:15]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:14])#[N:13]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 13614033Methyl 3-iodo-4-methylbenzoate

생성물 1

HCID 11819538Methyl 3-cyano-4-methylbenzoate

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5.7 g of methyl 3-iodo-4-methylbenzoate in 35 mL of DMF (degassed) was added 1.94 g (16.5 mmol) of Zn(CN)2 and 1.58 g (1.37 mmol) of Pd(PPh3)4. The mixture was stirred at 80° C. in the dark (with the light off) for 6 h. To the mixture was added 50 mL of 10% NH4OH (aq.) and EtOAc. The organic layer was washed with 50 mL of water and 30 mL of brine, and the combined aqueous layers were extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided about 3 g of methyl 3-cyano-4-methylbenzoate as a pale yellow solid.

후처리

  1. washThe organic layer was washed with 50 mL of water and 30 mL of brine
  2. extractionthe combined aqueous layers were extracted with EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-d6bcc60df98349ca9f6d3fb8a358f5a1
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299267B2

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