(2S)-1,1-Diphenyl-2-Allyloxy-Pent-4-en → (2S)-2-benzhydryl-3,6-dihydro-2H-pyran

HRID 78922Notes

Reaction equation

HRID 78922 reaction equation
C1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:8]([O:12][CH2:13][CH:14]=C)[CH2:9][CH:10]=C)C=CC=CC=1>C1C=CC=CC=1>[CH:7]([C@@H:8]1[CH2:9][CH:10]=[CH:14][CH2:13][O:12]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 11323419(2S)-1,1-Diphenyl-2-Allyloxy-Pent-4-en

Product 1

HCID 54762285(2S)-2-benzhydryl-3,6-dihydro-2H-pyranYield 176.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Into a solution of (2S)-1,1-Diphenyl-2-Allyloxy-Pent-4-ene 26a (0.19 g, 0.68 mmol) in dry benzene was added Grubb catalyst (0.028 g, 0.034 mmol, 5%) and the solution was refluxed under N2 for 20 h. The solvent was removed, and the residue was purified by flash chromatography (hexane/ether=9:1) to give 0.15 g (2S)-2-benzhydryl-3,6-dihydro-2H-pyran, 27a (88%, [α]D=(−)79.3, c=1, MeOH).

Workup

  1. temperaturethe solution was refluxed under N2 for 20 h
  2. customThe solvent was removed
  3. customthe residue was purified by flash chromatography (hexane/ether=9:1)

Sources & evidence

ORD record
ord-cf1c31fa7b784b6c8b1e4d6239d99dd6
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

Loading…