Ethanol → 3-Ethoxy-6-methoxybenzo[D]isoxazole

HRID 1171620

반응식

HRID 1171620 반응식
O1C2C=CC=C[C:4]=2[CH:3]=N1.[OH:10][C:11]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[O:13][N:12]=1.C(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:3]([O:10][C:11]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[O:13][N:12]=1)[CH3:4]

참가 물질

7

반응물 5

HCID 702EthanolHCID 11776TriphenylphosphineHCID 710731,2-BenzisoxazoleHCID 5363146Diisopropyl azodicarboxylateHCID 178487771HCID 178487771, 화합물

생성물 1

HCID 210778053-Ethoxy-6-methoxybenzo[D]isoxazole수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Benzisoxazole from part (b) (193 mg, 1.17 mmol), ethanol (75 μl, 1.29 mmol) and triphenylphosphine (460 mg, 1.75 mmol) were dissolved in anhydrous THF (4 ml) and cooled (0°). Diisopropylazodicarboxylate (345 μl, 1.75 mmol) was added slowly and after 10-15 min the reaction flask was removed from the ice bath and the reaction mixture was stirred at room temperature overnight under an argon atmosphere. The solution was evaporated to dryness and the residue pre-absorbed onto silica, and chromatographed on silica (19 g); eluent:hexane (300 ml), 10-30% ethyl acetate/hexane to give 3-ethoxy-6-methoxy-1,2-benzisoxazole (101 mg, 44%) as white crystals.

후처리

  1. temperaturecooled (0°)
  2. customwas removed from the ice bath
  3. customThe solution was evaporated to dryness
  4. customthe residue pre-absorbed onto silica
  5. customchromatographed on silica (19 g)

출처 및 근거

ORD 기록
ord-ebc2daa7fe7f40e59e89a011da98a52e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829705B2

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