Formaldehyde → 4-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one

HRID 1503420노트

반응식

HRID 1503420 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C=O.[C:14]1(B(O)O)C=CC=CC=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[CH2:14])[C:6]2=[O:11]

참가 물질

7

반응물 5

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 121749864-Fluoro-1-indanone

생성물 1

HCID 581981174-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one수율 72%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a 1000 mL round bottle flask were charged 4-fluoro-2,3-dihydro-1H-inden-1-one (249a) (5.04 g, 33.6 mmol), paraformaldehyde (10.08 g, 336 mmol), phenylboronic acid (4.92 g, 40.3 mmol) followed by toluene (235 mL), to the suspension was added TFA 2.6 mL, 33.6 mmol), and the resulting suspension was refluxed for 4 hrs, which resulted a clear yellowish solution. The solution was cooled to room temperature, and the pH was adjusted to 7-8 by adding saturated NaHCO3. After extracting with ethyl acetate, the organic layers were combined, and evaporated. The residue was purified by flash chromatography (0 to 30% EtOAc/Hexane) to give 4-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one (249b) (3.91 g, 72%). LC-MS tR=1.49 min in 3 min chromatography, MS (ESI) m/z 163 [M+H]+

후처리

  1. temperaturewas refluxed for 4 hrs
  2. customwhich resulted a clear yellowish solution
  3. extractionAfter extracting with ethyl acetate
  4. customevaporated
  5. customThe residue was purified by flash chromatography (0 to 30% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-102f4d77668f4d9fb0b658a56c432610
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212153B2

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