Dibenzofuran → Dibenzofuran, 4-methyl-

HRID 964565

반응식

HRID 964565 반응식
[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

참가 물질

6

반응물 4

HCID 568DibenzofuranHCID 6497Dimethyl SulfateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

생성물 1

HCID 43489Dibenzofuran, 4-methyl-수율 100.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-31779468f8784f4498be2fec604b723d
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770598

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