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 1108171Notes

Reaction equation

HRID 1108171 reaction equation
[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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6020ca88a7ff4736bb9407777889f576
Source dataset
uspto-grants-2000_05
Patent number
US06063360

Reaction notes

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