Cyclopropanecarbonitrile → 1-[2,6-Bis(methoxymethoxy)-3-methyl-phenyl]cyclopropanecarbonitrile

HRID 1484517ノート

反応式

HRID 1484517 の反応式
F[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[C:6]([CH3:12])[CH:5]=[CH:4][C:3]=1[O:13][CH2:14][O:15][CH3:16].[CH:17]1([C:20]#[N:21])[CH2:19][CH2:18]1.C[Si](N([K])[Si](C)(C)C)(C)C>C1(C)C=CC=CC=1>[CH3:11][O:10][CH2:9][O:8][C:7]1[C:6]([CH3:12])=[CH:5][CH:4]=[C:3]([O:13][CH2:14][O:15][CH3:16])[C:2]=1[C:17]1([C:20]#[N:21])[CH2:19][CH2:18]1

参加物

5

反応物 3

HCID 79637CyclopropanecarbonitrileHCID 727043342-Fluoro-1,3-bis(methoxymethoxy)-4-methyl-benzene2 回HCID 178504302HCID 178504302、化合物

生成物 1

HCID 900148221-[2,6-Bis(methoxymethoxy)-3-methyl-phenyl]cyclopropanecarbonitrile収率 42.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
105 °C

実験手順

2-fluoro-1,3-bis(methoxymethoxy)-4-methyl-benzene (Intermediate 34, 17.5 g, 76.011 mmol) and cyclopropanecarbonitrile (22.625 g, 337.23 mmol) were warmed under stirring to 105° C. A solution of [bis(trimethylsilyl)amino]potassium 0.5M in Toluene (275 ml) was slowly added for 1 hour to the previous solution. The reaction mixture was stirred for 6 hour at the same temperature. After cooling the solid was filtered off and the filtrate was partitioned between Brine (200 ml) and ethyl acetate (300 ml). The aqueous layer was re-extracted with ethyl acetate (200 ml) and combined organic layers were dried (Na2SO4), filtered and evaporated (the temperature during the concentration was ˜60° C. for removing the excess of cyclopropane carbonitrile). The residue was triturated with isopropanol (25 ml) and the solid collected and dried to afford the title compound (9.0 g) as white solid.

後処理

  1. stirringThe reaction mixture was stirred for 6 hour at the same temperature
  2. temperatureAfter cooling the solid
  3. filtrationwas filtered off
  4. customthe filtrate was partitioned between Brine (200 ml) and ethyl acetate (300 ml)
  5. extractionThe aqueous layer was re-extracted with ethyl acetate (200 ml)
  6. dry with materialwere dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated (the temperature during the concentration was ˜60° C.
  9. customfor removing the excess of cyclopropane carbonitrile)
  10. customThe residue was triturated with isopropanol (25 ml)
  11. customthe solid collected
  12. customdried

出典と根拠

ORDレコード
ord-d48bf122405f4ceaaae32918cf85162e
出典データセット
uspto-grants-2016_08
特許番号
US09422252B2

反応ノート

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