Bromomethylcyclopropane → Ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate

HRID 2190956Notes

Reaction equation

HRID 2190956 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[C:6]([CH:11]1[S:16][CH2:15][CH2:14][CH2:13][S:12]1)([O:8][CH2:9][CH3:10])=[O:7]>>[CH:5]1([CH2:4][C:11]2([C:6]([O:8][CH2:9][CH3:10])=[O:7])[S:12][CH2:13][CH2:14][CH2:15][S:16]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 88552Ethyl 1,3-dithiane-2-carboxylate

Product 1

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

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-ed6ffba63c2b44bba48163bed3a7a481
Source dataset
uspto-grants-2012_12
Patent number
US08324417B2

Reaction notes

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