(-)-Secoisolariciresinol → 3,4-Divanillyltetrahydrofuran

HRID 842324

反応式

HRID 842324 の反応式
[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

参加物

5

反応物 2

HCID 65373(-)-SecoisolariciresinolHCID 22619264Triphenyl phosphine chloride

生成物 1

HCID 1822103,4-Divanillyltetrahydrofuran収率 81%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

(−) 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.

後処理

  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

出典と根拠

ORDレコード
ord-9df280bb6dd545bfbb36d42525c2a215
出典データセット
uspto-grants-2002_04
特許番号
US06372922B1

関連ノート

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