Isopropanol hexane → (S)-styrene oxide

HRID 1513513Notes

Reaction equation

HRID 1513513 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[CH:8]([OH:10])[CH3:9]>C(Cl)(Cl)Cl>[C:3]1([C@H:9]2[CH2:8][O:10]2)[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 21585144Isopropanol hexane

Product 1

HCID 114946(S)-styrene oxideYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Colorless oily substance, 69% yield, >99% ee (CHIRALCEL OD-H, hexane/iPrOH 99.9:0.1); [α]D23 +26.1° (c=0.48, CHCl3); 1H NMR (CDCl3): δ7.39-7.26 (m, 5H), 3.88-3.85 (dd, J=2.6, 4.0 Hz, 1H), 3.17-3.13 (dd, J=4.0, 5.6 Hz, 1H), 2.82-2.79 ppm (dd, J=2.6, 5.6 Hz, 1H).

Sources & evidence

ORD record
ord-1aff6eb1d80d479ea5c70b3a6ad8b6ba
Source dataset
uspto-grants-2012_07
Patent number
US08217184B2

Reaction notes

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