Homoallyl bromide → Ethyl 2-methyl-2-(methylsulfonyl)hex-5-enoate

HRID 404213Notes

Reaction equation

HRID 404213 reaction equation
CS(C(C)C(OCC)=O)(=O)=O.BrCCC=C.[CH3:17][C:18]([S:28]([CH3:31])(=[O:30])=[O:29])([CH2:24][CH2:25][C:26]#[CH:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH3:17][C:18]([S:28]([CH3:31])(=[O:29])=[O:30])([CH2:24][CH2:25][CH:26]=[CH2:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 3

HCID 21241Homoallyl bromideHCID 10511577Ethyl 2-(methylsulfonyl)propanoateHCID 86709146Ethyl 2-methyl-2-(methylsulfonyl)hex-5-ynoate

Product 1

HCID 86709147Ethyl 2-methyl-2-(methylsulfonyl)hex-5-enoateYield 46%

Procedure

The title compound (8.0 g, 46%) was prepared from ethyl 2-(methylsulfonyl)propanoate (13.3 g, 74.1 mmol) and 4-bromobut-1-ene (10.0 g, 74.1 mmol) by following the procedure described for the synthesis of ethyl 2-methyl-2-(methylsulfonyl)hex-5-ynoate (Preparation 1, Step B). MS (GCMS) m/z 235 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ1.33 (t, J=7.17 Hz, 3H) 1.63 (s, 3H) 1.91-2.08 (m, 2H) 2.13-2.29 (m, 1H) 2.32 (d, J=7.51 Hz, 1H) 3.05 (s, 3H) 4.29 (q, J=7.06 Hz, 2H) 4.95-5.16 (m, 2H) 5.67-5.93 (m, 1H)

Sources & evidence

ORD record
ord-80dc8dfbebb548288036b941efa36042
Source dataset
uspto-grants-2014_06
Patent number
US08748466B2

Reaction notes

Loading…