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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
Notes
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Reaction equation

HRID 2595 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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, compound

Product 1

HCID 86752295
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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8a322f043809404b8fb31f9aa2d7aec3
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728370

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes