Isobutyryl chloride → 1-(2,6-Bis{[(methyloxy)methyl]oxy}phenyl)-2-methyl-1-propanone

HRID 527531ノート

反応式

HRID 527531 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][O:13][CH3:14])[CH:6]=1.[Li]CCCC.[CH3:20][CH:21]([CH3:25])[C:22](Cl)=[O:23]>C1COCC1.CCCCCC>[CH3:14][O:13][CH2:12][O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]=1[C:22](=[O:23])[CH:21]([CH3:25])[CH3:20]

参加物

6

反応物 3

HCID 62325Isobutyryl chlorideHCID 122226821,3-Bis(methoxymethoxy)benzene2 回HCID 178418339Butyllithium

生成物 1

HCID 679585761-(2,6-Bis{[(methyloxy)methyl]oxy}phenyl)-2-methyl-1-propanone収率 27.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

1,3-bis{[(methyloxy)methyl]oxy}benzene (Intermediate 35, 2.2 g) was dissolved under nitrogen in THF (8.0 mL) and a solution of BuLi (8.32 mL of a 1.6 M solution in hexane, 13.3 mmol) was added. After stirring at room temperature for 1 hour, cooling down to −78° C., 2-methylpropanoyl chloride (4.65 ml, 44.4 mmol) was added and the reaction mixture was stirred at that temperature for 1 hour. After quenching with water, the reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated. The residue obtained was then charged on a silica gel column (Biotage SP1 system) and eluted with Cyclohexane/EtOAc (from all 10/0 to 9/1, then 9/1, then from 9/1 to 8/2, then 8/2) to afford the title compound (825 mg).

後処理

  1. temperaturecooling down to −78° C.
  2. stirringthe reaction mixture was stirred at that temperature for 1 hour
  3. customAfter quenching with water
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe gathered organic layers were dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained
  9. additionwas then charged on a silica gel column (Biotage SP1 system)
  10. washeluted with Cyclohexane/EtOAc (from all 10/0 to 9/1

出典と根拠

ORDレコード
ord-a94f2a77d8834f1bbb28062d7d3a780c
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

読み込み中…