Pentane → 3-Benzylcyclopentan-1-one

HRID 991966

Reaction equation

HRID 991966 reaction equation
CC1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.[CH2:51]([C:58]1[CH2:62][CH2:61][C:60](=[O:63])[CH:59]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.CCCCC>C(OCC)C>[CH2:51]([CH:58]1[CH2:62][CH2:61][C:60](=[O:63])[CH2:59]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

5

Reactant 3

HCID 8003PentaneHCID 4189906(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthylHCID 118299173-Benzylcyclopent-2-en-1-one

Product 1

HCID 144001193-Benzylcyclopentan-1-oneYield 795.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

General procedure B using (S)-p-tol-BINAP and 3-benzylcyclopentenone (0.11 g, 0.7 mmol) gave, after 24 h at 0° C. and flash chromatography (6:1 pentane:diethyl ether), the title compound as a clear liquid (0.97 g, 85% yield). Spectroscopic data were consistent with previously reported data for this compound.12 [α]D25° C.−96° (c 1.3, CHCl3). Chiral HPLC analysis (Chiracel OD column) indicated that the title compound was obtained in 96% ee.

Workup

  1. customgave, after 24 h at 0° C.

Sources & evidence

ORD record
ord-8043dd963be74ac882008cdbdcd8c3d5
Source dataset
uspto-grants-2002_10
Patent number
US06465664B1

Linked notes

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