N-bromobutanimide → Ethyl 3-cyclopropyl-2-oxopropanoate

HRID 2190957Notes

Reaction equation

HRID 2190957 reaction equation
[CH:1]1([CH2:4][C:5]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])SCCCS2)[CH2:3][CH2:2]1.BrN1C(=[O:22])CCC1=O>>[CH:1]1([CH2:4][C:5](=[O:22])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 22285400Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

Product 1

HCID 22285629Ethyl 3-cyclopropyl-2-oxopropanoate

Procedure

Preferably R3 is methyl, ethyl or isopropyl. Most preferably R3 is ethyl and the compound of Formula 5 is prepared by (a) reacting bromomethylcyclopropane with 2-carboethoxy-1,3-dithiane in the presence of a strong base to give ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate; (b) reacting the ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate with N-bromosuccinimide to give ethyl 3-cyclopropyl-2-oxopropanoate; and (c) reacting the ethyl 3-cyclopropyl-2-oxopropanoate with bis(2-methoxyethyl)aminosulfur trifluoride.

Sources & evidence

ORD record
ord-bbad51cb4f134562af410074a71e83fe
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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