Sodium Chloride → Methyl 6-(hydroxymethyl)picolinate

HRID 744180

반응식

HRID 744180 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11](C2C=CC=CC=2)(C2C=CC=CC=2)[O:12][SiH2]C(C)(C)C)[N:6]=1)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Cl-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][OH:12])[N:6]=1)=[O:4]

참가 물질

5

반응물 3

HCID 5234Sodium ChlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131719562HCID 131719562, 화합물

생성물 1

HCID 11513809Methyl 6-(hydroxymethyl)picolinate수율 63.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3.52 g of 6-(diphenyl-tert-butylsilyloxymethyl)-2-pyridinecarboxylic acid methyl ester in 87 ml of tetrahydrofuran is mixed at 24° C. under nitrogen with 13.6 g of tetrabutylammonium fluoride-trihydrate and stirred for 2 hours. Then, it is mixed with 32 ml of concentrated sodium chloride solution and extracted four times with ethyl acetate. The combined organic phases are dried on sodium sulfate and after filtration, concentrated by evaporation in a vacuum. The thus obtained residue is purified by chromatography on silica gel. With hexane/50-100% ethyl acetate, 0.92 g of the title compound is obtained as colorless oil.

후처리

  1. extractionextracted four times with ethyl acetate
  2. customThe combined organic phases are dried on sodium sulfate
  3. filtrationafter filtration
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe thus obtained residue is purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-bfa52026e7254c26b24c3bde7aea5814
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559134

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