2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiole → 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

HRID 1108169ノート

反応式

HRID 1108169 の反応式
[CH3:1][C:2]1([CH3:16])[S:6][C:5]2[CH:7]=[C:8]3[S:12][C:11]([CH3:14])([CH3:13])[S:10][C:9]3=[CH:15][C:4]=2[S:3]1.[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].C[O:23][C:24]([C:26]1[C:36]2[O:37][C:38]([CH3:41])([CH3:40])[O:39][C:35]=2[CH:34]=[C:28]2[O:29][C:30]([CH3:33])([CH3:32])[O:31][C:27]=12)=O>C1COCC1>[CH3:13][C:11]1([CH3:14])[S:10][C:9]2[C:15]([C:24]([C:17]3[C:5]4[S:6][C:2]([CH3:16])([CH3:1])[S:3][C:4]=4[CH:20]=[C:19]4[S:12][C:11]([CH3:13])([CH3:14])[S:10][C:18]=34)([C:26]3[C:27]4[O:31][C:30]([CH3:32])([CH3:33])[O:29][C:28]=4[CH:34]=[C:35]4[O:39][C:38]([CH3:40])([CH3:41])[O:37][C:36]=34)[OH:23])=[C:4]3[S:3][C:2]([CH3:16])([CH3:1])[S:6][C:5]3=[CH:7][C:8]=2[S:12]1

参加物

5

反応物 3

HCID 111969402,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithioleHCID 206693184-Methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis-(1,3)-dioxoleHCID 178418339Butyllithium

生成物 1

HCID 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)methanol収率 44%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dithiole (2.86 g, 10 mmol; prepared according to WO-91/12024) was dissolved in anhydrous THF (75 mL) and cooled to -70° C. n-Butyllithium (4.4 mL, 2.5M in hexane) was added. The reaction mixture was allowed to reach ambient temperature. 4-Methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis-(1,3)-dioxole (1.4 g, 5 mmol) was added as a solid. After 1 hour, the mixture was quenched with saturated aqueous NaH2PO4. The aqueous phase was discarded and the organic layer evaporated. The residue was dissolved in dichloromethane, washed with water and dried (Na2SO4). The product was purified by column chromatography (dichloromethane:heptane, 1:1) giving 1.8 g (44%) of pure product.

後処理

  1. customprepared
  2. additionwas added
  3. customto reach ambient temperature
  4. customthe mixture was quenched with saturated aqueous NaH2PO4
  5. customthe organic layer evaporated
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washwashed with water
  8. dry with materialdried (Na2SO4)
  9. customThe product was purified by column chromatography (dichloromethane:heptane, 1:1)

出典と根拠

ORDレコード
ord-eabfeb1131614797bc63a6377f50a960
出典データセット
uspto-grants-2000_05
特許番号
US06063360

反応ノート

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