Tetrahydrofuran → Biphenyl

HRID 704163Notes

Reaction equation

HRID 704163 reaction equation
O1[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].[C].C1(C)C=CC=CC=1>[C:2]1([C:3]2[CH:2]=[CH:5][CH:4]=[CH:5][CH:4]=2)[CH:3]=[CH:2][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

1.31 g (3 mmol) of II-23 was mixed with 10 ml of tetrahydrofuran, 3 ml of toluene and 0.1 g of 2% Pd-carbon, and the mixture was subjected to catalytic hydrogenation in a hydrogen atmosphere. The reaction mixture was filtered to remove the catalyst and further treated and purified according to Example 21 to obtain 0.32 g (31% yield) of (+)-4-hydroxy-4'-(1-2's,3's-2-chloro-3-methylpentanoyl)ethyl)biphenyl. [α]D25 =+60° (c=1, CHCl3), m.p.=99°-100° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. additionfurther treated
  4. custompurified

Sources & evidence

ORD record
ord-45f0d2f2be7c442d8b320bd0a663fc67
Source dataset
uspto-grants-1991_01
Patent number
US04985590

Reaction notes

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