(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanol → (1r)-1-Methylthiocarbonyloxyethyl-2-methylpropanoate

HRID 558060Notes

Reaction equation

HRID 558060 reaction equation
[CH3:1][C:2]([O:4][CH:5]([O:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[CH3:6])=[S:3].FC(F)(F)[C@@H](C1C2C(C=C3C=1C=CC=C3)=CC=CC=2)O>>[CH3:1][C:2]([O:4][C@@H:5]([O:7][C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[CH3:6])=[S:3]

Participants

3

Reactant 2

HCID 7006444(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanolHCID 871835061-(Methylthiocarbonyloxy)ethyl isobutyrate

Product 1

HCID 87183618(1r)-1-Methylthiocarbonyloxyethyl-2-methylpropanoate

Procedure

For comparison, racemic 1-methylthiocarbonyloxyethyl-2-methylpropanoate: 1H-NMR in presence of (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol as chiral solvating agent (CDCl3): δ 1.18 (m, 6H), 1.49 (d, J=5.2 Hz, 1.5H), 1.50 (d, J=5.6 Hz, 1.5H), 2.33 (s, 1.5H), 2.34 (s, 1.5H), 2.55 (septet, J=7.2 Hz, 0.5H), 2.56 (septet, J=7.2 Hz, 0.5H), 6.92 (q, J=5.6 Hz, 0.5H), 6.92 (q, J=5.6 Hz, 0.5H) ppm.

Sources & evidence

ORD record
ord-7823fc5bae31412db73fc13829aadb6c
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

Loading…