(-)-Secoisolariciresinol → 3,4-Divanillyltetrahydrofuran

HRID 842323

반응식

HRID 842323 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].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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

4

반응물 2

HCID 65373(-)-SecoisolariciresinolHCID 22470945Triphenylphosphine bromide

생성물 1

HCID 1822103,4-Divanillyltetrahydrofuran수율 82.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
40 °C

실험 절차

(−) secoisolariciresinol (100 mg) was dissolved in acetonitrile (5 ml) and to it was added a solution of triphenyl phosphine bromide 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 silica gel column. Elution of the column with 30% EtOAC in pet. ether gave (−) 3,4-divanillyl tetrahydrofuran (78 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 silica gel column
  5. washElution of the column with 30% EtOAC in pet. ether

출처 및 근거

ORD 기록
ord-32746da895a94177bc01be364712e60a
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372922B1

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