(-)-Secoisolariciresinol → 3,4-Divanillyltetrahydrofuran

HRID 842323

Reaction equation

HRID 842323 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].[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

Participants

4

Reactant 2

HCID 65373(-)-SecoisolariciresinolHCID 22470945Triphenylphosphine bromide

Product 1

HCID 1822103,4-DivanillyltetrahydrofuranYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
40 °C

Procedure

(−) 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.

Workup

  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

Sources & evidence

ORD record
ord-32746da895a94177bc01be364712e60a
Source dataset
uspto-grants-2002_04
Patent number
US06372922B1

Linked notes

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