Ethyl 2-formylbutanoate → HCID 51029584, compound

HRID 2171741Notes

Reaction equation

HRID 2171741 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][CH2:13][CH:14]3[O:18][C:17]([NH2:19])=[N:16][CH2:15]3)[CH:5]=[CH:4][C:3]1=2.C([O:23][C:24](=O)[CH:25]([CH:28]=O)[CH2:26][CH3:27])C>C(O)C>[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][CH2:13][C@H:14]3[O:18][C:17]4=[N:19][C:24](=[O:23])[C:25]([CH2:26][CH3:27])=[CH:28][N:16]4[CH2:15]3)[CH:5]=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 289299Ethyl 2-formylbutanoateHCID 67053798HCID 67053798, compound

Product 1

HCID 51029584HCID 51029584, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.5 g, 1.82 mmol) in ethanol (16 mL) was added 2-formyl-butyric acid ethyl ester (0.39 g, 2.7 mmol). The reaction mixture was stirred at room temperature for one hour, and then heated at reflux for 24 hours. It was then concentrated and loaded on a silica gel column. Chromatography with (1-5%) 2-propanol/methylene chloride gave 0.15 g the title product. [α]D25=−26.8 (c=0.74, CHCl3).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. concentrationIt was then concentrated

Sources & evidence

ORD record
ord-784585f0491a4810bf794b5f4a77cf0b
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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