Lithium Hexamethyldisilazide → HCID 69204168, compound

HRID 583441Notes

Reaction equation

HRID 583441 reaction equation
COC1C=C(C(C2C=CC(OC)=C(OC)C=2)=CC(OC)=O)C=CC=1OC.[CH2:27]([O:29][C:30]1[CH:31]=[C:32]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=O)[CH3:28].C([N:48](CC)[C:49]([CH2:51]P(=O)([O-])[O-])=[O:50])C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[C:35]1([C:33]([C:32]2[CH:41]=[CH:42][C:43]([O:44][CH3:45])=[C:30]([O:29][CH2:27][CH3:28])[CH:31]=2)=[CH:51][C:49]([NH2:48])=[O:50])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 4

HCID 2733832Lithium HexamethyldisilazideHCID 9820154Methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylateHCID 14297383HCID 14297383, compoundHCID 21584592HCID 21584592, compound

Product 1

HCID 69204168HCID 69204168, compound

Procedure

The acrylamide was prepared analogously to methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate using 3-ethoxy-4-methoxybenzophenone (0.3 g, 1.2 mmol), diethylcarbamoylmethylphosphonate (0.25 g, 1.3 mmol) and lithium hexamethyldisilazide (1 mL, 1.3 mmol, 1.3M) with a reaction time of 54 hours at reflux. The crude mixture was purified by flash column chromatography (silica gel, 45% ethyl acetate/methylene chloride) to afford 0.06 g (17%) of a mixture of the E and Z isomers as an oil: 1H NMR (CDCl3) δ 7.54-7.19 (m, 10H), 7.00-6.65 (m, 6H), 6.34 (s, 2H), 5.54 (s, 1H), 5.55 (s, 1H), 5.24 (s, 1H ), 5.04 (s, 1H), 4.16 (m, 4H), 3.92 (s, 3H), 3.87 (s, 3H), 1.60-1.33 (m, 6H); 13C NMR (CDCl3) δ 168.7, 168.6, 150.8, 150.4, 149.7, 148.4, 148.0, 140.7, 138.2, 133.0, 130.2, 129.2, 129.1, 128.8, 128.3, 128.0, 121.9, 121.6, 120.0, 113.7, 111.9, 111.4, 110.8, 64.4, 64.3, 55.9, 14.6; Anal. Calcd for C18H19NO3.0.35H2O. Theoretical: C, 71.19; H, 6.54; N, 4.61. Found: C, 71.19; H, 6.68; N, 4.45.

Workup

  1. customwith a reaction time of 54 hours
  2. temperatureat reflux
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 45% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-e1ee9023d0214095b99e684d8c8410a7
Source dataset
uspto-grants-1999_07
Patent number
US05929117

Reaction notes

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