Ethyl Acetate → (2R)-(+)-Trans-3-(3-bromophenyl)oxiranemethanol

HRID 2393703Notes

Reaction equation

HRID 2393703 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.C(OCC)(=[O:14])C>>[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:14][C@@H:9]2[CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 186764783-(3-Bromophenyl)-2-propen-1-ol

Product 1

HCID 18665090(2R)-(+)-Trans-3-(3-bromophenyl)oxiranemethanolYield 73%

Procedure

The title compound was prepared from trans-3-(3-bromophenyl)-2-propenol by a sequence analogous to that described above for compound (9a) but using D-(-)-diethyl tartrate. Column chromatography (ethyl acetate--light petroleum (b.p. 40°-60° C.), 3:7) provided the title compound (73%) as a pale yellow oil. Distilled at 160°-185° C. at 0.1 mmHg. using a Kugelrohr short path distillation apparatus as a colourless oil; [α]D25 +37.6 (c=0.020 gml-1, CHCl3).

Sources & evidence

ORD record
ord-e8f8c35589934e8e8fafd8bb329f0d8c
Source dataset
uspto-grants-1998_09
Patent number
US05807866

Reaction notes

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