Nitric Acid → (3R,3aR,6S,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diyl diacetate

HRID 462130

반응식

HRID 462130 반응식
[CH2:1]1[O:5][C@@H:4]2[C@@H:6](O)[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([O:14][C:15](=[O:17])[CH3:16])(=O)[CH3:12].[N+]([O-])(O)=[O:19]>>[CH3:16][C:15]([O:14][C@H:11]1[C@H:1]2[O:5][CH2:4][C@H:3]([O:8][C:7]([CH3:6])=[O:19])[C@H:2]2[O:10][CH2:12]1)=[O:17]

참가 물질

4

반응물 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12597Isosorbide

생성물 1

HCID 11770257(3R,3aR,6S,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diyl diacetate

실험 절차

Either one of the above residues containing the mixture of the 2-acetate, 5-acetate and 2,5-diacetate of 1,4:3,6-dianhydro-D-glucitol is nitrated. The preferred nitration method is to add slowly the residue over a period of 0.1 to 5 hours to a solution at -5° to 25° C, preferably 0° to 5° C, of one to 20 molar equivalents, preferably three to five molar equivalents, of acetic anhydride and one to ten molar equivalents, preferably one to two molar equivalents, of nitric acid. After the addition is completed, the reaction mixture is stirred for about 0.5 to 2 hours at -5° to 25° C, preferably 0° to 5° C, in order to complete the nitration. In this manner a solution containing a mixture of 1,4:3,6-dianhydro-D-glucitol 5-acetate 2-nitrate, 1,4:3,6-dianhydro-D-glucitol 2-acetate 5-nitrate and 1,4:3,6-dianhydro-D-glucitol 2,5-diacetate is obtained.

후처리

  1. additionEither one of the above residues containing
  2. additionto add slowly the residue over a period of 0.1 to 5 hours to a solution at -5° to 25° C
  3. custompreferably 0° to 5° C
  4. additionAfter the addition
  5. additionIn this manner a solution containing

출처 및 근거

ORD 기록
ord-c7240821e75f4326b1c3544b08dd135f
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04065488

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