2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole) → Tris(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol

HRID 1450040ノート

反応式

HRID 1450040 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.C([Li])CCC.[CH3:22][C:23]1([CH3:55])[O:27][C:26]2[C:28]([C:37]([C:39]3[C:49]4[O:50][C:51]([CH3:54])([CH3:53])[O:52][C:48]=4[CH:47]=[C:41]4[O:42][C:43]([CH3:46])([CH3:45])[O:44][C:40]=34)=[O:38])=[C:29]3[O:33][C:32]([CH3:35])([CH3:34])[O:31][C:30]3=[CH:36][C:25]=2[O:24]1>C1COCC1>[CH3:13][C:11]1([CH3:14])[O:10][C:9]2[C:15]([C:37]([C:28]3[C:26]4[O:27][C:23]([CH3:55])([CH3:22])[O:24][C:25]=4[CH:36]=[C:30]4[O:31][C:32]([CH3:35])([CH3:34])[O:33][C:29]=34)([C:39]3[C:49]4[O:50][C:51]([CH3:53])([CH3:54])[O:52][C:48]=4[CH:47]=[C:41]4[O:42][C:43]([CH3:45])([CH3:46])[O:44][C:40]=34)[OH:38])=[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

5

反応物 3

HCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 18943092Bis(2,2,6,6-tetramethylbenzo-(1,2-d:4,5-d']bis(1,3)dioxole-4-yl)ketoneHCID 178418339Butyllithium

生成物 1

HCID 10952571Tris(2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)methanol

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)dioxole (8.80 g, 40.00 mmol, Example 5) was dissolved in THF (100 mL) and cooled to -20° C. n-Butyllithium (25.0 mL, 40.0 mmol, 1.6M) was added and the temperature was adjusted to ambient temperature over a period of 30 minutes and then recooled to -20° C. Bis(2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d']bis(1,3)dioxole-4-yl)ketone (18.80 g, 39.83 mmol, Example 57) was added and the temperature was once more adjusted to room temperature and the mixture was stirred for 18 hours. The mixture was then poured on water/AcOH (100 mL, 2% AcOH) and extracted with diethyl ether (2×100 mL). The organic phase was washed with water (2×100 ml) and dried (Na2SO4). The solvent was evaporated and the product was washed with petroleum ether (20 mL, 40°-60° C.). Yield 10.80 g (64.1%). Spectral data see example 44.

後処理

  1. additionwas added
  2. customrecooled to -20° C
  3. customwas once more adjusted to room temperature
  4. additionThe mixture was then poured on water/AcOH (100 mL, 2% AcOH)
  5. extractionextracted with diethyl ether (2×100 mL)
  6. washThe organic phase was washed with water (2×100 ml)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated
  9. washthe product was washed with petroleum ether (20 mL, 40°-60° C.)

出典と根拠

ORDレコード
ord-3b59da73ed354d938dfa020edd1ffbe0
出典データセット
uspto-grants-1997_02
特許番号
US05599522

反応ノート

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