Pentane → HCID 22676882, compound

HRID 1006187Notes

Reaction equation

HRID 1006187 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]([O:58][CH:59]([CH3:68])[CH2:60][CH2:61][C:62]1[C:63](=[O:67])[CH2:64][CH2:65][CH:66]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.CCCCC>C(OCC)C>[CH2:51]([O:58][CH:59]([CH3:68])[CH2:60][CH2:61][CH:62]1[CH2:66][CH2:65][CH2:64][C:63]1=[O:67])[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 22676876HCID 22676876, compound

Product 1

HCID 22676882HCID 22676882, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

General procedure B using (S)-p-tol-BINAP and 3-benzyloxybutyl-cyclopent-2-enone (0.146 g, 0.6 mmol) gave, after 30 h at 0° C. and flash chromatography (1:2 pentane:diethyl ether), the title compound as a clear oil (0.139 g, 94% yield). 1H NMR (300 MHz, CDCl3): δ 7.37-7.23 (m, 5H), 4.50 (s, 2H), 3.47 (t, J=6.3 Hz, 2H), 2.43-2.04 (m, 5H), 1.78 (ddd, J=18.0, 9.6, 1.2 Hz, 1H), 1.70-1.56 (m, 2H), 1.56-1.34 (m, 5H). 13C NMR (75 MHz, CDCl3): δ 219.8, 138.6, 128.4, 127.7, 127.6, 73.1, 70.3, 45.4, 38.7, 37.4, 35.7, 30.0, 29.7, 24.8. IR (neat): 2934, 2860, 1741, 1455, 1405, 1363, 1158, 1100, 737, 699 cm−1. HRMS m/z calcd for C16H22O2 246.1620, obsd 246.1615. [α]D25° C.−89° (c 1.4, CHCl3). Chiral HPLC analysis (Chiracel OD column) indicated that the title compound was obtained in 94% ee.

Workup

  1. customgave, after 30 h at 0° C.

Sources & evidence

ORD record
ord-a1aa58be3b5f4c86ab1003f91125471a
Source dataset
uspto-grants-2004_09
Patent number
US06787655B2

Reaction notes

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