(-)-Secoisolariciresinol → 3,4-Divanillyltetrahydrofuran

HRID 842324

Reaction equation

HRID 842324 reaction equation
[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

Participants

5

Reactant 2

HCID 65373(-)-SecoisolariciresinolHCID 22619264Triphenyl phosphine chloride

Product 1

HCID 1822103,4-DivanillyltetrahydrofuranYield 81%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

(−) 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.

Workup

  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

Sources & evidence

ORD record
ord-9df280bb6dd545bfbb36d42525c2a215
Source dataset
uspto-grants-2002_04
Patent number
US06372922B1

Linked notes

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