Water → 4-Formyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole

HRID 400293ノート

反応式

HRID 400293 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.CN([CH:25]=[O:26])C.O>C1COCC1.C1(C)C=CC=CC=1.CC(O)=O>[CH:25]([C:15]1[C:4]2[O:3][C:2]([CH3:16])([CH3:1])[O:6][C:5]=2[CH:7]=[C:8]2[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]=12)=[O:26]

参加物

8

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 178418339Butyllithium

生成物 1

HCID 189430854-Formyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole (20.0 g, 90 mmol (Example 5)) was dissolved in THF (300 mL) and cooled to -20° C. n-Butyl lithium (38.0 mL), 2.5M in toluene, 100 mmol) was added and the temperature was allowed to rise to 0° C. The mixture was recooled to -20° C. and DMF (6.9 mL, 90.0 mmol) was added. The reaction mixture was stirred over night while allowing the temperature to increase to room temperature. Water (200 mL) and AcOH (5 mL) was added. The color changed from light yellow to strong orange. The mixture was extracted with diethyl ether (3×300 mL) and the combined organic phase was washed with water (2×100 mL), dried (Na2SO4) and evaporated. The product was trituated twice with petroleum ether and dried, yielding the pure title compound; 16.3 g (72%).

後処理

  1. addition100 mmol) was added
  2. customto rise to 0° C
  3. customwas recooled to -20° C.
  4. extractionThe mixture was extracted with diethyl ether (3×300 mL)
  5. washthe combined organic phase was washed with water (2×100 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customdried

出典と根拠

ORDレコード
ord-dd7f0da26e6c47c7aa9717727054899d
出典データセット
uspto-grants-1998_10
特許番号
US05827501

反応ノート

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