p-Toluenesulfonic acid monohydrate → tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one

HRID 6057노트

반응식

HRID 6057 반응식
C([C@H](C(O)CC([O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)CCCCCCCCCCC)C(O)=O)CCCCC.[OH2:33].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>C(O)C>[OH:33][C@@H:31]1[CH2:30][CH2:29][CH:28]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:34][CH3:44])[O:27][C:26]1=[O:25]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 678557542-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid

생성물 1

HCID 67855761tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

M)a) 15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid were dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulfonic acid monohydrate were added. The reaction mixture was heated to 55°-60° C. until the reaction was finished. The solvent was removed in vacuo and the residue was dissolved in 160 ml of dichloromethane. The solution was stirred at room temperature for 1 hour. The reaction mixture was evaporated. The material obtained was chromatographed on silica gel. There was obtained tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one, m.p. 95°-96° C.

후처리

  1. temperatureThe reaction mixture was heated to 55°-60° C. until the reaction
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 160 ml of dichloromethane
  4. customThe reaction mixture was evaporated
  5. customThe material obtained
  6. customwas chromatographed on silica gel

출처 및 근거

ORD 기록
ord-79667b592cd94ca2943c996933ceac25
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246960

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