Dibenzofuran → Dibenzofuran, 4-methyl-

HRID 964565

反応式

HRID 964565 の反応式
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:14]([Li])CCC.S(OC)(OC)(=O)=O.[Cl-].[NH4+]>C1COCC1>[CH3:14][C:4]1[C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][CH:3]=1

参加物

6

反応物 4

HCID 568DibenzofuranHCID 6497Dimethyl SulfateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

生成物 1

HCID 43489Dibenzofuran, 4-methyl-収率 100.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Dibenzofuran (26.94 g, 160 mmol) was dissolved in dry THF (500 ml) and cooled to -78° C. n-Butyl lithium (1.6M in hexane, 200 ml, 320 mmol) was added in portions over 30 mins. and the solution was allowed to warm to room temperature over 2.5 hours. The solution was recooled to -70° C. and a mixture of dimethyl sulphate (32 ml, 340 mmol) in dry THF (100 ml) was added dropwise. Once the addition was complete, the reaction was allowed to warm to room temperature, stirred for 18 hours and poured onto saturated ammonium chloride solution (400 ml). The phases were separated and the aqueous extracted twice with ether. The combined organic phases were dried (MgSO4) and evaporated in vacuo. Chromatography on silica (eluting with 40-60 petrol) gave the pure product as a clear oil (29.2 g, 100%) δH [2H6 ]-DMSO 8.1 (1H, d), 7.9 (1H, d), 7.7 (1H, d),7.5 (1H, t), 7.4 (1H, t), 7.25 (2H, m), 2.55 (3H, s).

後処理

  1. additionwas added in portions over 30 mins
  2. customwas recooled to -70° C.
  3. additionwas added dropwise
  4. additionOnce the addition
  5. temperatureto warm to room temperature
  6. customThe phases were separated
  7. extractionthe aqueous extracted twice with ether
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-31779468f8784f4498be2fec604b723d
出典データセット
uspto-grants-1998_06
特許番号
US05770598

関連ノート

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