Water → 4-(Methoxycarbonyl)bicyclo(2.2.1)heptane-1-carboxylic acid

HRID 1854333

反応式

HRID 1854333 の反応式
[C:1]12([C:12]([O:14]C)=[O:13])[CH2:7][C:4]([C:8]([O:10][CH3:11])=[O:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[OH-].[K+].O>CO>[CH3:11][O:10][C:8]([C:4]12[CH2:7][C:1]([C:12]([OH:14])=[O:13])([CH2:6][CH2:5]1)[CH2:2][CH2:3]2)=[O:9]

参加物

5

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13633974Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate

生成物 1

HCID 137617744-(Methoxycarbonyl)bicyclo(2.2.1)heptane-1-carboxylic acid収率 71%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate (2.00 g, 9.44 mmol, as prepared in Aust. J. Chem., 1985, 38, 1705-18) in MeOH (47 mL) was added KOH (0.475 g, 8.46 mmol) and water (2.5 mL). The reaction was stirred at reflux for about 16 h and then cooled to room temperature and concentrated to dryness under reduced pressure. Water (25 mL) was added to the remaining residue and the mixture was extracted with Et2O (2×25 mL). The aqueous layer was acidified to about pH 4 using aqueous 6 N HCl and was extracted with DCM (3×20 mL). The combined DCM extracts were dried over anhydrous MgSO4, filtered, and concentrated to provide 4-(methoxycarbonyl)bicyclo[2.2.1]heptane-1-carboxylic acid as an off-white solid (1.19 g, 71%): 1H NMR (400 MHz, DMSO-d6) δ 12.19 (s, 1H), 3.61 (s, 3H), 1.92 (d, J=6.6 Hz, 4H), 1.76 (s, 2H), 1.65-1.54 (m, 4H).

後処理

  1. temperatureat reflux for about 16 h
  2. concentrationconcentrated to dryness under reduced pressure
  3. additionWater (25 mL) was added to the remaining residue
  4. extractionthe mixture was extracted with Et2O (2×25 mL)
  5. extractionwas extracted with DCM (3×20 mL)
  6. dry with materialThe combined DCM extracts were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ed7d91009e4a44fea4f7993cab8aa30a
出典データセット
uspto-grants-2015_02
特許番号
US08962629B2

関連ノート

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