Water → Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)methanol

HRID 2597노트

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HRID 2597 반응식
[CH3:1][C:2]1([CH3:16])[O:6][C:5]2[CH:7]=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].CO[C:24]([C:26]1[C:36]2[S:37][C:38]([CH3:41])([CH3:40])[S:39][C:35]=2[CH:34]=[C:28]2[S:29][C:30]([CH3:33])([CH3:32])[S:31][C:27]=12)=[O:25].[OH2:42]>CCOCC>[CH3:13][C:11]1([CH3:14])[O:10][C:9]2[C:15]([C:24]([C:17]3[C:5]4[O:6][C:2]([CH3:16])([CH3:1])[O:3][C:4]=4[CH:20]=[C:19]4[O:42][C:9]([CH3:15])([CH3:8])[O:10][C:18]=34)([C:26]3[C:36]4[S:37][C:38]([CH3:40])([CH3:41])[S:39][C:35]=4[CH:34]=[C:28]4[S:29][C:30]([CH3:32])([CH3:33])[S:31][C:27]=34)[OH:25])=[C:4]3[O:3][C:2]([CH3:16])([CH3:1])[O:6][C:5]3=[CH:7][C:8]=2[O:12]1

참가 물질

6

반응물 4

HCID 962WaterHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 539241844-Methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)HCID 178418339Butyllithium

생성물 1

HCID 86752296Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)methanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

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온도
0 °C

실험 절차

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole (5.15 g, 23.2 mmol) was dissolved in dry ether (40.0 mL) in a dried, argon filled reaction vessel. The solution was cooled to 0° C. and n-butyllithium (9.29 mL, 2.5M in hexane) was added. After stirring for 15 min at ambient temperature, the mixture was cooled to 0° C. and 4-methoxycarbonyl-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole)(4.0 g, 11.6 mmol) was added portionwise. The reaction was stirred at ambient temperature overnight. The voluminous precipitate was dissolved by addition of water (70 mL) and ether (50 mL). The organic layer was separated and the aqueous phase was washed once more with ether. The organic phase was dried (Na2SO4) and evaporated to give a semisolid residue. The product was recrystallized from acetonitrile. Yield of pure product was 5.26 g (60%).

후처리

  1. additionfilled
  2. customreaction vessel
  3. temperaturethe mixture was cooled to 0° C.
  4. stirringThe reaction was stirred at ambient temperature overnight
  5. customThe organic layer was separated
  6. washthe aqueous phase was washed once more with ether
  7. dry with materialThe organic phase was dried (Na2SO4)
  8. customevaporated
  9. customto give a semisolid residue
  10. customThe product was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-760fc340b5b24bef86b0fc2c43979b8e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728370

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