Tetrahydrofuran → ACMC-20apjz

HRID 225354

反応式

HRID 225354 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 3690897ACMC-20apjz

試薬・触媒・溶媒 3

HCID 159722Silver tetrafluoroborate触媒HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dd869fdce46747399b17ca2efa36c7da
出典データセット
uspto-grants-1980_11
特許番号
US04236027

関連ノート

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