(-)-Secoisolariciresinol → 3,4-Divanillyltetrahydrofuran

HRID 842324

반응식

HRID 842324 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][C@H:10]([C@H:13]([CH2:24]O)[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH2:11][OH:12])[CH:6]=[CH:5][C:4]=1[OH:26].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(#N)C>[CH2:9]([CH:10]1[CH:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH2:24][O:12][CH2:11]1)[C:7]1[CH:6]=[CH:5][C:4]([OH:26])=[C:3]([O:2][CH3:1])[CH:8]=1

참가 물질

5

반응물 2

HCID 65373(-)-SecoisolariciresinolHCID 22619264Triphenyl phosphine chloride

생성물 1

HCID 1822103,4-Divanillyltetrahydrofuran수율 81%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

(−) secoisolariciresinol (100 mg,) was dissolved in THF (5 ml) and to it was added a solution of triphenyl phosphine chloride in acetonitrile (1 ml) and the mixture was stirred at 0-80° C. for 1-10 hours. After completion of the reaction, the reaction mixture was concentrated under vacuum and the residue thus obtained was chromatographed over florosil column. Elution of the column with 30% EtOAC in pet. ether gave (−-3,4-divanillyl tetrahydrofuran (77 mg), m.p. 114-116° C.

후처리

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customthe residue thus obtained
  4. customwas chromatographed over florosil column
  5. washElution of the column with 30% EtOAC in pet. ether

출처 및 근거

ORD 기록
ord-9df280bb6dd545bfbb36d42525c2a215
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372922B1

연결된 노트

불러오는 중…