Potassium Hydroxide → 3(R)-hydroxy-2-methylene-3-phenylpropanoic Acid

HRID 9781

反応式

HRID 9781 の反応式
[OH-].[K+].[OH:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[CH2:10])[C:6]([O:8]C)=[O:7]>O.CO>[OH:3][C@H:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[CH2:10])[C:6]([OH:8])=[O:7]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 9942369Methyl 3-Hydroxy-2-methylene-3-phenylpropionate

生成物 1

HCID 120136653(R)-hydroxy-2-methylene-3-phenylpropanoic Acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of potassium hydroxide (2.65 g, 0.047 mol, 1.3 eq) in water (60 mL) was added drop wise to a solution of 1b (7 g, 0.036 mol, 1 eq) in methanol (20 mL) (see FIG. 5). The mixture was stirred at room temperature for 15 h. The solution was then concentrated under vacuum. The aqueous phase was washed with ether (2×100 mL), acidified with 6N aqueous HCl solution and extracted with ether (3×100 mL). The combined organic extracts were washed with brine (100 mL) and dried over sodium sulfate. Evaporation of the solvent afforded a colorless oil which crystallized upon standing. The desired product 9b was obtained as a solid (6.29 g, 97%). Rf 0.26 (hexane/EtOAc=6:4). 1H NMR δ (DMSO-d6) 5.41 (s, 1H), 5.61 (s, 1H), 5.93 (s, 1H), 6.15 (s, 1H), 7.22 (m, 5H), 12.45 (s, 1H). [M−H]− 177.1, tR=1.23 min; purity: 91%.

後処理

  1. concentrationThe solution was then concentrated under vacuum
  2. washThe aqueous phase was washed with ether (2×100 mL)
  3. extractionextracted with ether (3×100 mL)
  4. washThe combined organic extracts were washed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent
  7. customafforded a colorless oil which
  8. customcrystallized

出典と根拠

ORDレコード
ord-8f64186500de404a9bed21e70c5814fb
出典データセット
uspto-grants-2006_08
特許番号
US07091354B2

関連ノート

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