Potassium Hydroxide → (2R,3R)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid

HRID 1478622Notes

Reaction equation

[O:1]1[C@@H:3]([C:4]([O:6]CC)=[O:5])[C@@H:2]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[OH-].[K+]>>[CH2:12]([O:11][C:9]([C@@H:2]1[O:1][C@H:3]1[C:4]([OH:6])=[O:5])=[O:10])[CH3:13]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 27336462,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylate

Product 1

HCID 13150798(2R,3R)-3-(ethoxycarbonyl)oxirane-2-carboxylic acidYield 73.5%

Procedure

Followed general procedure for 4 using the following quantities: 3b (15.2 g, 81 mmol): KOH (4.53 g, 81 mmol, in EtOH [50 ml]); yielded 5 as a colorless oil (9.5 g, 73.5%). 1H NMR (CDCl3, 400 MHz): δ 7.57 (br, 1H); 4.35-4.24 (m, 2H); 3.73 (s, 1H); 3.72 (s, 1H); 1.36-1.32 (t 3H). 13C NMR (CDCl3, 100 MHz): 171.61, 166.40, 62.45, 52.20, 51.45, 13.89.

Sources & evidence

ORD record: ord-f22de3460e6149169b5dff18a55d6d15
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403843B2

Reaction notes

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