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

反応式

HRID 2595 の反応式
[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]

参加物

6

反応物 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、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8a322f043809404b8fb31f9aa2d7aec3
出典データセット
uspto-grants-1998_03
特許番号
US05728370

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