Acetone → 9-(3-Hydroxy-5-oxocyclopent-1-EN-1-YL)nonanoic acid

HRID 1439096ノート

反応式

HRID 1439096 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][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:3]1.CC(C)=[O:21].O>[B-](F)(F)(F)F.[Ag+].CO>[OH:21][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:3]1

参加物

6

反応物 3

HCID 180AcetoneHCID 962WaterHCID 204656274-Bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one

生成物 1

HCID 132897909-(3-Hydroxy-5-oxocyclopent-1-EN-1-YL)nonanoic acid

試薬・触媒・溶媒 2

HCID 159722Silver tetrafluoroborate触媒HCID 887Methanol溶媒

実験手順

To a stirred solution of 57.2 g. of crude 4-bromo-2-(8-carboxyoctyl)cyclopent-2-en-1-one (Example 100) in 500 ml. of acetone and 325 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during a 15 minute period. The mixture is stirred at 0°-3° C. for 2 hours and filtered. The filtrate is diluted with water, saturated with solid sodium chloride, and extracted with ether. The extract is washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Partition chromatography of the residue on Celite gives white crystals, m.p. 58°-66° C., λ max.MeOH = 223 mμ (7800); ν max (KBR) = 3340 (hydroxyl groups), 1705 (carbonyl groups), and 1625 cm-1 (olefin group).

後処理

  1. filtrationfiltered
  2. additionThe filtrate is diluted with water, saturated with solid sodium chloride
  3. extractionextracted with ether
  4. washThe extract is washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customPartition chromatography of the residue on Celite
  8. customgives white crystals, m.p. 58°-66° C., λ max

出典と根拠

ORDレコード
ord-3690cadc8dc6403c935b89b7ef089395
出典データセット
uspto-grants-1977_11
特許番号
USRE029469

反応ノート

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