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 2597ノート

反応式

HRID 2597 の反応式
[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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-760fc340b5b24bef86b0fc2c43979b8e
出典データセット
uspto-grants-1998_03
特許番号
US05728370

反応ノート

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