2-Bromopropionic acid → HCID 21069793, compound

HRID 348104Notes

Reaction equation

[CH3:1][S:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Br[CH:9]([CH3:13])[C:10]([OH:12])=[O:11]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][CH:9]([CH3:13])[C:10]([OH:12])=[O:11]

Participants

Reactant 3

HCID 117292-Bromopropionic acid

HCID 24758Sodium hydride

HCID 789252-(Methylthio)ethanol

Product 1

HCID 21069793HCID 21069793, compoundYield 78%

Procedure

Addition of 2-methylthioethanol (10.0 g, 0.108 mol) to sodium hydride (9.54 g of a 60% dispersion in mineral oil, 0.238 mol, washed twice with hexane) followed by reaction with 2-bromopropionic acid (16.6 g, 0.108 mol) gave 13.81 g (78% yield) of the title compound as a clear oil; bp 80–90° C./0.2 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ ppm: 1.49 (3H, d, J=7.0 Hz, CH3), 2.18 (3H, s, SCH3), 2.76 (2H, t, J=6.6 Hz, CH2), 3.74 (2H, t, J=6.6 Hz, CH2), 4.07 (1H, d, J=7.0 Hz, OCH).

Workup

washwashed twice with hexane)

Sources & evidence

ORD record: ord-d73afb7f1c8b4084bf5d3ac5ae3b02ba
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176196B2

Reaction notes

Loading…