Benzene → 2-benzhydryl-3,4-dihydro-2H-pyran

HRID 1429015Notes

Reaction equation

HRID 1429015 reaction equation
C1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]([O:13][CH:14]=C)[CH2:9][CH2:10][CH:11]=C)C=CC=CC=1.[CH:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH:7]([CH:8]1[CH2:9][CH2:10][CH:11]=[CH:14][O:13]1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 241BenzeneHCID 666312581,1-Diphenyl-2-(1-ethenoxy)-hex-5-ene

Product 1

HCID 666312272-benzhydryl-3,4-dihydro-2H-pyranYield 92.6%

Reagents, catalysts & solvents 1

HCID 178479819HCID 178479819, compoundCatalyst

Procedure

A solution of 1,1-diphenyl-2-(1-ethenoxy)-hex-5-ene 9 (5.1 g, 18.3 mmol) and Grubb's catalyst (1.5 g, 1.83 mmol) in benzene (200 ml) was heated under reflux for 20 hr. The solvent was removed under vacuo and the residue was chromatographed over silica gel (Hexane/Ethyl Acetate 20:1) to give 2-diphenyl-3,4-dihydro-2H-pyran 10 (4.25 g, 92.6%) as a liquid.

Workup

  1. temperatureunder reflux for 20 hr
  2. customThe solvent was removed under vacuo
  3. customthe residue was chromatographed over silica gel (Hexane/Ethyl Acetate 20:1)

Sources & evidence

ORD record
ord-907d8110b680433f82eda0a78f5e97d3
Source dataset
uspto-grants-2015_01
Patent number
US08937189B2

Reaction notes

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