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

HRID 2594노트

반응식

HRID 2594 반응식
[CH3:1][C:2]1([CH3:16])[S:6][C:5]2[CH:7]=[C:8]3[S:12][C:11]([CH3:14])([CH3:13])[S:10][C:9]3=[CH:15][C:4]=2[S:3]1.[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].C[O:23][C:24]([C:26]1[C:36]2[O:37][C:38]([CH3:41])([CH3:40])[O:39][C:35]=2[CH:34]=[C:28]2[O:29][C:30]([CH3:33])([CH3:32])[O:31][C:27]=12)=O>C1COCC1>[CH3:13][C:11]1([CH3:14])[S:10][C:9]2[C:15]([C:24]([C:17]3[C:5]4[S:6][C:2]([CH3:16])([CH3:1])[S:3][C:4]=4[CH:20]=[C:19]4[S:12][C:11]([CH3:13])([CH3:14])[S:10][C:18]=34)([C:26]3[C:27]4[O:31][C:30]([CH3:32])([CH3:33])[O:29][C:28]=4[CH:34]=[C:35]4[O:39][C:38]([CH3:40])([CH3:41])[O:37][C:36]=34)[OH:23])=[C:4]3[S:3][C:2]([CH3:16])([CH3:1])[S:6][C:5]3=[CH:7][C:8]=2[S:12]1

참가 물질

5

반응물 3

HCID 111969402,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithioleHCID 206693184-Methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis-(1,3)-dioxoleHCID 178418339Butyllithium

생성물 1

HCID 86752294Bis-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)-mono-(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)methanol수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dithiole (2.86 g, 10 mmol; prepared according to WO-91/12024) was dissolved in anhydrous THF (75 mL) and cooled to -70° C. n-Butyllithium (4.4 mL, 2.5M in hexane) was added. The reaction mixture was allowed to reach ambient temperature. 4-Methoxycarbonyl-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d')-bis-(1,3)-dioxole (1.4 g, 5 mmol) was added as a solid. After 1 hour, the mixture was quenched with saturated aqueous NaH2PO4. The aqueous phase was discarded and the organic layer evaporated. The residue was dissolved in dichloromethane, washed with water and dried (Na2SO4). The product was purified by column chromatography (dichloromethane:heptane, 1:1) giving 1.8 g (44%) of pure product.

후처리

  1. customprepared
  2. additionwas added
  3. customto reach ambient temperature
  4. customthe mixture was quenched with saturated aqueous NaH2PO4
  5. customthe organic layer evaporated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialdried (Na2SO4)
  9. customThe product was purified by column chromatography (dichloromethane:heptane, 1:1)

출처 및 근거

ORD 기록
ord-6735643c3b9e41779184084c922223ce
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728370

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