Acetic Acid → 4-(3-Pyridylmethyl)benzoic acid methyl ester

HRID 2058513노트

반응식

HRID 2058513 반응식
COC(=O)/C=C/C1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1.[C-:20]#N.[Na+].[C:23]([OH:26])(=[O:25])[CH3:24]>[O-2].[O-2].[Mn+4].CO>[CH3:20][O:25][C:23](=[O:26])[C:24]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

생성물 1

HCID 541209054-(3-Pyridylmethyl)benzoic acid methyl ester

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 887Methanol용매

실험 절차

A mixture of 300 mg of the aldehyde(prepared as described in Reference Example 1), 370 mg of sodium cyanide, 3.0 g of manganese dioxide, 0.18 ml of acetic acid and 15 ml of methanol was stirred overnight at room temperature, filtered through a pad of infusorial earth, and the filtrate was concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate, and extracted with chloroform. The extract was washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (3:2) as eluent to give 255 mg of the title compound having the following physical characteristics:

후처리

  1. filtrationfiltered through a pad of infusorial earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of cyclohexane and ethyl acetate (3:2) as eluent

출처 및 근거

ORD 기록
ord-99a8c332728542708ea84a011411e766
출처 데이터셋
uspto-grants-1982_03
특허 번호
US04317828

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