Dimethylformamide dimethyl acetal → 1-(Adamantan-1-yl)-3-(dimethylamino)prop-2-en-1-one

HRID 1197631Notes

Reaction equation

HRID 1197631 reaction equation
[CH3:1][C:2]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)=[O:3].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[C:4]12([C:2](=[O:3])[CH:1]=[CH:16][N:17]([CH3:19])[CH3:18])[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketone

Product 1

HCID 27473581-(Adamantan-1-yl)-3-(dimethylamino)prop-2-en-1-oneYield 37%

Procedure

A solution of 17.83 g (0.10 mol) of 1-adamantyl methyl ketone in 35.75 g (0.30 mol) of dimethylformamide dimethylacetal was heated at reflux for 24 hours. After cooling and removal of the solvent in vacuo at 45° to 50° C., the residue was purified by silical gel chromatography to yield 8.64 g (37%) of a white solid: Rf 0.20 in 50% EtOAc/Ligroin; 1H NMR (CDCl3) δ 1.68 (S, 6H, the δ hydrogens of the adamantyl ring, methylene protons at the farthest position from the substituent), 1.81 (S, 6H, the β hydrogens of the adamantyl ring, methylene protons at the closest position to the substituent), 2.00 (S, 3H, the three bridgehead protons, 2.90 (br S, 6H, N(CH3)2), 5.20 (d, 1H, J=14 Hz, O=C-CH), 7.60 (d 1H, J=14 Hz, =C-N<). All analytical data confirmed the assigned structure.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling
  3. customremoval of the solvent in vacuo at 45° to 50° C.
  4. customthe residue was purified by silical gel chromatography

Sources & evidence

ORD record
ord-eba1206fa1424b1db2a4fadb1b3b39b3
Source dataset
uspto-grants-1994_01
Patent number
US05276158

Reaction notes

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