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

HRID 9781

반응식

HRID 9781 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-8f64186500de404a9bed21e70c5814fb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091354B2

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