Sodium Chloride → 3-Ethoxybenzo[D]isoxazol-6-OL

HRID 624095노트

반응식

HRID 624095 반응식
B(Br)(Br)Br.O1C2C=CC=CC=2C=N1.[CH2:14]([O:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([O:26]C)=[CH:25][C:20]=2[O:19][N:18]=1)[CH3:15].C([O-])(O)=O.[Na+].[Na+].[Cl-]>ClCCl.O.CCCCCC.C(OCC)(=O)C>[CH2:14]([O:16][C:17]1[C:21]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:20]=2[O:19][N:18]=1)[CH3:15]

참가 물질

9

반응물 5

HCID 5234Sodium ChlorideHCID 25134Boron tribromideHCID 710731,2-BenzisoxazoleHCID 516892Sodium BicarbonateHCID 210778053-Ethoxy-6-methoxybenzo[D]isoxazole

생성물 1

HCID 1358487453-Ethoxybenzo[D]isoxazol-6-OL

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

Boron tribromide (1.0M solution in dichloromethane; 1.39 ml, 1.39 mmol) was added to a stirred, −78° cooled solution of benzisoxazole from part (c) (179 mg, 928 μmol) in dichloromethane (4 ml) under an argon atmosphere. The reaction mixture was gradually warmed to room temperature over approx. 2 hours, and stirred overnight. Tlc (silica, 2:1 hexane/ethyl acetate) showed new polar material as well as unreacted starting material. The reaction was worked up by adding water (5 ml) and ice. The aqueous phase was neutralized by addition of saturated NaHCO3 solution, and saturated with NaCl. The aqueous phase was extracted into dichloromethane (3×60 ml), then the organic extracts combined and washed with brine (10 ml) and dried (NaSO4). The product was purified by chromatography on silica (18 g; eluent 2.5%, 5%, then 15% ethyl acetate/hexane). The first compound to elute was unreacted 3-ethoxy-6-methoxy-1,2-benzisoxazole, (46 mg), followed by 3-ethoxy-6-hydroxy-1,2-benzisoxazole 108 mg (65%).

후처리

  1. extractionThe aqueous phase was extracted into dichloromethane (3×60 ml)
  2. washwashed with brine (10 ml)
  3. dry with materialdried (NaSO4)
  4. customThe product was purified by chromatography on silica (18 g
  5. washThe first compound to elute

출처 및 근거

ORD 기록
ord-9476a652b6ae44bd815590dc7a24602b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303026B2

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