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Hydrochloric Acid → (E)-3-cyclopropyl-2-(4-(methoxymethoxy)phenyl)-3-phenylacrylic acid

HRID 884065
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HRID 884065 반응식
[CH:1]1(/[C:4](/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:5](/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[CH:13][CH:12]=2)\[C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO>[CH:1]1(/[C:4](/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:5](/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][O:19][CH3:20])=[CH:13][CH:12]=2)\[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86630293(E)-Ethyl 3-cyclopropyl-2-(4-(methoxymethoxy)phenyl)-3-phenylacrylate

생성물 1

HCID 68733087(E)-3-cyclopropyl-2-(4-(methoxymethoxy)phenyl)-3-phenylacrylic acid수율 75%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

To a solution of 3 (105 mg, 0.298 mmol) in MeOH (3 ml) was added 2N NaOH (1.5 ml), and the mixture was stirred at 80° C. for 24 h. After cooling, 2 N HCl (1.5 ml) was added drop wise under ice cooling, and the whole was extracted with AcOEt, the organic layer was washed with brine, dried over Na2SO4, then concentrated. The residual solid was triturated with hexanes to give 7 (75%). 7: colorless powder; 1H-NMR (CDCl3) δ 0.45 (2H, m), 0.83 (2H, m), 2.73 (1H, m), 3.40 (3H, s), 5.04 (2H, s), 6.73 (2H, d, J=9.0 Hz), 6.89 (2H, m), 6.92 (2H, d, J=9.0 Hz), 7.05-7.14 (3H, m).

후처리

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with AcOEt
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residual solid was triturated with hexanes

출처 및 근거

ORD 기록
ord-415988ff5a554d0abc71eab9152c1777
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236987B2

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