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

HRID 400293노트

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HRID 400293 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-dd7f0da26e6c47c7aa9717727054899d
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827501

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