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

HRID 1741960ノート

反応式

HRID 1741960 の反応式
[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]

参加物

8

反応物 4

HCID 962Water2 回HCID 7628Boric Acid2 回HCID 677933994,5-(Dimethylmethylenedioxy)-6-(methoxymethoxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazoleHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 887Methanol溶媒3 回HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-78f8f89f5c9847ee8377414053f4096e
出典データセット
uspto-grants-1994_08
特許番号
US05334740

反応ノート

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