Tetrahydrofuran → ACMC-20apjz

HRID 225354

반응식

HRID 225354 반응식
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.[O:17]1CCCC1>O.CCOCC.[B-](F)(F)(F)F.[Ag+]>[OH:17][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1

참가 물질

6

반응물 2

HCID 8028TetrahydrofuranHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

생성물 1

HCID 3690897ACMC-20apjz

시약·촉매·용매 3

HCID 159722Silver tetrafluoroborate촉매HCID 962Water용매2회HCID 3283Diethyl Ether용매

실험 절차

To a stirred solution of 56.0 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 400 ml. of tetrahydrofuran and 133 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during 25 minutes. The mixture is stirred at 0°-5° C. for 60 minutes, diluted with water and ether, and filtered. The aqueous portion of the filtrate is saturated with solid sodium chloride and extracted with additional ether. The combined organic phases are washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Column chromatography of the residue gives the subject compound as a mixture with 4-hydroxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one, NMR(CDCl3) 3.60 (multiplet, O-methylene hydrogens) and 4.60 (multiplet, O-methine hydrogen).

후처리

  1. filtrationfiltered
  2. extractionextracted with additional ether
  3. washThe combined organic phases are washed successively with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dd869fdce46747399b17ca2efa36c7da
출처 데이터셋
uspto-grants-1980_11
특허 번호
US04236027

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