Dimethylformamide → 1,1'-Biphenyl, 2,2'-bis(methoxymethoxy)-

HRID 859081

반응식

HRID 859081 반응식
[H-].[Na+].CN(C=O)C.[C:8]1([OH:21])[C:9]([C:14]2[C:15]([OH:20])=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1.[CH3:22][O:23][CH2:24]Cl.C1[CH2:30][O:29][CH2:28]C1>>[CH3:22][O:23][CH2:24][O:21][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH2:28][O:29][CH3:30]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 8028Tetrahydrofuran2회HCID 15731(1,1'-Biphenyl)-2,2'-diolHCID 24758Sodium hydride

생성물 1

HCID 114713211,1'-Biphenyl, 2,2'-bis(methoxymethoxy)-수율 97%

실험 절차

To a 250 mL of three-necked bottle was added NaH (content 50%, 3.5 g, 72 mmol), anhydrous THF (60 mL) and anhydrous DMF (20 mL), after the temperature was lowered to 0° C., a solution of biphenol (5.6 g, 30 mmol) in THF (15 mL) was added, stirred at this temperature for 10 minutes. Methoxymethyl chloride (6 mL, 78 mmol) was added dropwise, and the mixture was stirred for 8 h at room temperature, quenched by adding 100 mL of water, extracted with ethyl acetate (100 mL×3), the combined organic phase was washed with brine (60 mL×2), dried over MgSO4, after filtration, the solvent was removed to give a yellow oil. Purification through chromatography give 8 g (97% yield) of the product as a light yellow oil. 1HNMR (300 MHz, CDCl3) δ (ppm) 3.39 (s, 6H), 5.12 (s, 4H), 7.13 (m, 2H), 7.30–7.37 (m, 6H). Physical data of the compound was consistent with that reported in literature.

후처리

  1. customwas lowered to 0° C.
  2. stirringthe mixture was stirred for 8 h at room temperature
  3. customquenched
  4. additionby adding 100 mL of water
  5. extractionextracted with ethyl acetate (100 mL×3)
  6. washthe combined organic phase was washed with brine (60 mL×2)
  7. dry with materialdried over MgSO4
  8. filtrationafter filtration
  9. customthe solvent was removed
  10. customto give a yellow oil
  11. customPurification through chromatography

출처 및 근거

ORD 기록
ord-d4e93b93b1a240b8be74ac423b42f8aa
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151070B2

연결된 노트

불러오는 중…