Water → 2-Hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone

HRID 1741960노트

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HRID 1741960 반응식
[OH2:1].B(O)(O)O.[H][H].[CH3:8][C:9]1([CH3:25])[O:24][CH:12]2[CH:13]([O:20][CH2:21][O:22][CH3:23])[CH2:14][C:15]3[CH:16]([CH2:17][O:18]N=3)[CH:11]2[O:10]1>[Ni].CO.C(OCC)C>[OH:18][CH2:17][CH:16]1[CH:11]2[O:10][C:9]([CH3:25])([CH3:8])[O:24][CH:12]2[CH:13]([O:20][CH2:21][O:22][CH3:23])[CH2:14][C:15]1=[O:1]

참가 물질

8

반응물 4

HCID 962Water2회HCID 7628Boric Acid2회HCID 677933994,5-(Dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 190110002-Hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone수율 61%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 887Methanol용매3회HCID 3283Diethyl Ether용매

실험 절차

Raney nickel W-2 (NDHF-90: a trademark for a product of Kawaken Fine Chemical K.K.; 550 mg) was subjected to decantation once with water and once with methanol. Forty eight milligrams of boric acid were added. The atmosphere was replaced with argon and then with hydrogen. Methanol (1.5 ml) and water (0.3 ml) were added and boric acid was dissolved therein. Then, a solution of 80 mg of 4,5-(dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole in 3.5 ml of methanol was added at room temperature, and the mixture was stirred for 5 hours. The reaction mixture was diluted with diethyl ether and filtered through florisel. The filtrate was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to afford 49 mg of 2-hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(methoxymethoxy)cyclohexanone having the following properties (yield 61%).

후처리

  1. filtrationfiltered through florisel
  2. washThe filtrate was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-78f8f89f5c9847ee8377414053f4096e
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334740

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