Dimethylformamide → 2-[2-(Adamantan-1-yloxy)-acetyl]-3-dimethylamino-acrylic acid benzyl ester

HRID 967795Notes

Reaction equation

HRID 967795 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C:11](=[O:24])[CH2:12][O:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][N:27]([CH:29]=O)[CH3:28]>O>[CH2:1]([O:8][C:9](=[O:25])[C:10]([C:11](=[O:24])[CH2:12][O:13][C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)=[CH:26][N:27]([CH3:29])[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 697440854-(Adamantan-1-yloxy)-3-oxo-butyric acid benzyl ester

Product 1

HCID 697980742-[2-(Adamantan-1-yloxy)-acetyl]-3-dimethylamino-acrylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-(adamantan-1-yloxy)-3-oxo-butyric acid benzyl ester (1.133 g, 3.3 mmol) and DMF dimethylacetal (0.56 mL, 3.96 mmol) in DMF (20 mL) was heated at 100° C. for 3 h. The mixture was diluted with H2O (80 mL) and extracted with EtOAc (2×30 mL). The combined extracts were washed with brine (2×30 mL), and dried (MgSO4). Filtration and evaporation of the solvent afforded the product, (0.647 g, 49%).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined extracts were washed with brine (2×30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and evaporation of the solvent
  5. customafforded the product, (0.647 g, 49%)

Sources & evidence

ORD record
ord-2bad9ce2406d4b72a7e8ac668de1b6f1
Source dataset
uspto-grants-2005_10
Patent number
US06956053B2

Reaction notes

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