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Toluene → 2-(Iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran

HRID 1850411
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HRID 1850411 반응식
C(=O)([O-])[O-].[Ca+2].I(Cl)(=O)=O.[I:10](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C1(C)C=CC=CC=1.[CH3:32][C:33]1[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[C:35]([CH2:41][C:42]([CH3:44])=[CH2:43])[C:34]=1[OH:45]>CO>[I:10][CH2:43][C:42]1([CH3:44])[CH2:41][C:35]2[C:36]([CH3:40])=[CH:37][C:38]([CH3:39])=[C:33]([CH3:32])[C:34]=2[O:45]1
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참가 물질

6

반응물 4

HCID 1140TolueneHCID 10112Calcium CarbonateHCID 10655310Phenol, 2,3,5-trimethyl-6-(2-methyl-2-propenyl)-HCID 56924451Trimethylbenzylammonium Dichloroiodate

생성물 1

HCID 152683052-(Iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran수율 183.4%

시약·촉매·용매 1

HCID 887
Methanol
용매

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온도
0 °C

실험 절차

Calcium carbonate (1.37 g, 13.7 mmol) and benzyltrimethylammonium dichloroiodate (4.04 g, 11.6 mmol) were sequentially added to a solution of toluene (20 mL)/methanol (10 mL) containing 2,3,5-trimethyl-6-(2-methylprop-2-en-1-yl)phenol (1.00 g, 5.26 mmol) synthesized in Reference Example 2 under ice-cooling condition, and the mixture was stirred at 0° C. for 30 minutes. After that, the reaction solution was concentrated under reduced pressure, and water and ethyl acetate were added to the residue to separate an organic layer. The organic layer was washed with 10% sodium sulfite aqueous solution and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0-95:5) to give 3.05 g of the title compound (yield: 92%).

후처리

  1. customsynthesized in Reference Example 2 under ice-
  2. temperaturecooling condition
  3. concentrationAfter that, the reaction solution was concentrated under reduced pressure, and water and ethyl acetate
  4. additionwere added to the residue
  5. customto separate an organic layer
  6. washThe organic layer was washed with 10% sodium sulfite aqueous solution and saturated saline
  7. customdried
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 100:0-95:5)

출처 및 근거

ORD 기록
ord-7ae8b2ef83f54becbcd5ce6ac0577012
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957069B2

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