Lithium Hexamethyldisilazide → HCID 69204168, compound

HRID 366599Notes

Reaction equation

HRID 366599 reaction equation
COC1C=C(C(C2C=CC(OC)=C(OC)C=2)=CC([O-])=O)C=CC=1OC.[CH2:26]([O:28][C:29]1[CH:30]=[C:31]([CH:40]=[CH:41][C:42]=1[O:43][CH3:44])[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=O)[CH3:27].C([N:47](CC)[C:48]([CH2:50]P(=O)([O-])[O-])=[O:49])C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[C:34]1([C:32]([C:31]2[CH:40]=[CH:41][C:42]([O:43][CH3:44])=[C:29]([O:28][CH2:26][CH3:27])[CH:30]=2)=[CH:50][C:48]([NH2:47])=[O:49])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 4

HCID 2733832Lithium HexamethyldisilazideHCID 14297383HCID 14297383, compoundHCID 21584592HCID 21584592, compoundHCID 21584610HCID 21584610, compound

Product 1

HCID 69204168HCID 69204168, compound

Procedure

The acrylamide was prepared analogously to 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, 10 H), 7.00-6.65 (m, 6 H), 6.34 (s, 2 H), 5.54 (s, 1 H), 5.55 (s, 1 H), 5.24 (s, 1 H), 5.04 (s, 1 H), 4.16 (m, 4 H), 3.92 (s, 3 H), 3.87 (s, 3 H), 1.60-1.33 (m, 6 H); 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-b8506c88b9634d4684f38ee74b336c64
Source dataset
uspto-grants-2000_10
Patent number
US06130226

Reaction notes

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