Ethyl 2-formylbutanoate → HCID 67053799, compound

HRID 2171738Notes

Reaction equation

HRID 2171738 reaction equation
[CH3:1][C:2]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14]2)([CH:4]1[O:8][C:7]([NH2:9])=[N:6][CH2:5]1)[CH3:3].C([O:22][C:23](=O)[CH:24]([CH:27]=O)[CH2:25][CH3:26])C>C(O)C>[CH3:3][C:2]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14]2)([C@H:4]1[O:8][C:7]2=[N:9][C:23](=[O:22])[C:24]([CH2:25][CH3:26])=[CH:27][N:6]2[CH2:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 289299Ethyl 2-formylbutanoateHCID 67053820HCID 67053820, compound

Product 1

HCID 67053799HCID 67053799, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(1,1-dimethyl-indan-5-yloxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.41 g, 1.57 mmol) in ethanol (16 mL) was added 2-formyl-butyric acid ethyl ester (0.34 g, 2.23 mmol). The reaction mixture was heated at reflux for 20 hours. It was then concentrated and loaded on a silica gel column. Chromatography with (1-5%) 2-propanol/methylene chloride gave 0.092 g of the title product. [α]D25=−24.1 (c=0.76, CHCl3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. concentrationIt was then concentrated

Sources & evidence

ORD record
ord-1835496aa5b84155bfcd38cf5fe29d9a
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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