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

HRID 473002ノート

反応式

HRID 473002 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-81204a30f56c4039b4c1fd6abc0a74e0
出典データセット
uspto-grants-2014_01
特許番号
US08633212B2

反応ノート

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