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Sodium Hydroxide → 2-((1-(Trifluoromethyl)cyclopropyl)methyl)malonic acid

HRID 1049282
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HRID 1049282 반응식
[F:1][C:2]([F:21])([F:20])[C:3]1([CH2:6][CH:7]([C:14]([O:16]C(C)C)=[O:15])[C:8]([O:10]C(C)C)=[O:9])[CH2:5][CH2:4]1.[OH-].[Na+]>CO.O1CCOCC1.O>[F:1][C:2]([F:20])([F:21])[C:3]1([CH2:6][CH:7]([C:14]([OH:16])=[O:15])[C:8]([OH:10])=[O:9])[CH2:5][CH2:4]1
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참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 90403930Diisopropyl 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonate

생성물 1

HCID 904024822-((1-(Trifluoromethyl)cyclopropyl)methyl)malonic acid수율 101.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 31275
1,4-Dioxane
용매

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온도
40 °C

실험 절차

A solution of diisopropyl 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonate (1.53 g, 4.93 mmol) in MeOH (10 mL), dioxane (10 mL) and H2O (10 mL) was treated with NaOH (1.183 g, 29.6 mmol) and heated at 40° C. overnight. The mixture was cooled to RT, the organics removed under reduced pressure, the aqueous residue acidified with 3M HCl, extracted with DCM and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 2-((1-(trifluoromethyl)cyclopropyl)methyl)malonic acid (1.13 g, 101%). 1H NMR (400 MHz, DMSO-d6): δ 12.91 (s, 2H), 3.36-3.34 (t, J=7.09 Hz, 1H), 2.08 (d, J=7.0 Hz, 2H), 0.88 (m, 2H), 0.77 (m, 2H).

후처리

  1. temperatureThe mixture was cooled to RT
  2. customthe organics removed under reduced pressure
  3. extractionextracted with DCM
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-3af87404ad1a49a9a480ec21cd80d605
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382228B2

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