Diethyl Carbonate → Bis-(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)-mono-(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)methanol

HRID 2595

반응식

HRID 2595 반응식
[CH3:1][C:2]1([CH3:50])[S:6][C:5]2[C:7]([C:16]([C:34]3[C:44]4[S:45][C:46]([CH3:49])([CH3:48])[S:47][C:43]=4[CH:42]=[C:36]4[S:37][C:38]([CH3:41])([CH3:40])[S:39][C:35]=34)([C:18]3[C:28]4[O:29][C:30]([CH3:33])([CH3:32])[O:31][C:27]=4[CH:26]=[C:20]4[O:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=34)[OH:17])=[C:8]3[S:12][C:11]([CH3:14])([CH3:13])[S:10][C:9]3=[CH:15][C:4]=2[S:3]1.[C:51]([Li])([CH3:54])(C)C.CN([CH2:59][CH2:60]N(C)C)C.[C:64](=[O:71])([O:68][CH2:69][CH3:70])OCC>C1C=CC=CC=1>[CH2:69]([O:68][C:64]([C:42]1[C:36]2[S:37][C:38]([CH3:41])([CH3:40])[S:39][C:35]=2[C:34]([C:16]([C:7]2[C:5]3[S:6][C:2]([CH3:50])([CH3:1])[S:3][C:4]=3[C:15]([C:30]([O:31][CH2:51][CH3:54])=[O:29])=[C:9]3[S:10][C:11]([CH3:13])([CH3:14])[S:12][C:8]=23)([C:18]2[C:19]3[O:23][C:22]([CH3:24])([CH3:25])[O:21][C:20]=3[C:26]([C:22]([O:23][CH2:59][CH3:60])=[O:21])=[C:27]3[O:31][C:30]([CH3:32])([CH3:33])[O:29][C:28]=23)[OH:17])=[C:44]2[C:43]=1[S:47][C:46]([CH3:49])([CH3:48])[S:45]2)=[O:71])[CH3:70]

참가 물질

6

반응물 4

HCID 7766Diethyl CarbonateHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 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)methanolHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 86752295Bis-(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole-4-yl)-mono-(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)methanol

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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 (0.50 g, 0.61 mmol) was dissolved in dry benzene (6.0 mL) under an atmosphere of argon. t-Butyllitium (2.44 mL, 1.5M in pentane) and TMEDA (0.545 mL, 3.66 mmol) were added. The reaction mixture was subjected to ultrasound for 25 min. and was then slowly added to a solution of diethyl carbonate (7.2 mL, 59.4 mmol) in dry benzene (16 mL). After stirring for 1.5 h, aqueous NaH2PO4 (50 mL) was added. The organic layer was separated, washed with water, dried (Na2SO4) and evaporated. After purification by preparative HPLC 130.0 mg (21%)) of the pure product was obtained. 1H NMR (CDCl3, 300 MHz) δ: 4.98 (s, 1H), 4.28-4.37 (m, 6H), 1.48-1.79 (m, 36H), 1.46 (t, 6H, J 7.0 Hz), 1.38 (t, 3H, J 7.0 Hz).

후처리

  1. customultrasound for 25 min.
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customAfter purification by preparative HPLC 130.0 mg (21%)) of the pure product
  7. customwas obtained

출처 및 근거

ORD 기록
ord-8a322f043809404b8fb31f9aa2d7aec3
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728370

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