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

HRID 78895

Reaction equation

HRID 78895 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-610562bf6af8475e806557347a3cbda5
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Linked notes

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