Potassium Carbonate → HCID 11485672, compound

HRID 2100190Notes

Reaction equation

HRID 2100190 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]#[N:35]>CC(C)=O>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([C:10](=[C:4]2[CH2:3][C:2]([CH3:25])([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5]2)[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:33][C:34]#[N:35])=[CH:15][CH:16]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68654510HCID 68654510, compound

Product 1

HCID 11485672HCID 11485672, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The O-alkylation procedure described for 190 was used. To a stirred suspension of 4,4′-[(3,3,5,5-tetramethylcyclohexylidene) methanediyl]diphenol (219) (0.600 g, 1.78 mmol), K2CO3 (0.368 g, 2.67 mmol), and acetone (60 mL) was added bromoacetonitrile (0.200 mL, 2.85 mmol) under a nitrogen atmosphere at RT. The reaction mixture was refluxed for 3 h, cooled to RT and filtered. Standard work-up followed by purification afforded 0.196 g (29%) of the title compound 229 as a white solid along with 0.38 g (52%) of the bis-alkylated compound 2,2′-[[(3,3,5,5-tetramethylcyclohexylidene) methanediyl]bis(benzene-4,1-diyloxy)]diacetonitrile. In addition, 0.10 g of unreacted starting material (219) was recovered. 1H NMR (300 MHz, CDCl3): δ 7.15 (d, J=8.7 Hz, 2H), 7.04 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 6.76 (d, J=8.4 Hz, 2H), 4.75 (s, 2H), 2.00 (s, 2H), 1.98 (s, 2H), 1.31 (s, 2H), 0.95 (s, 12H). LCMS (ESI): m/z 374 (M−H)−. Anal. Calcd for C25H29NO2, C, 79.96; H, 7.78; N, 3.73; Found: C, 79.95; H, 7.84; N, 3.73.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. filtrationfiltered
  3. customStandard work-up followed by purification

Sources & evidence

ORD record
ord-cec2eef28eaf48f0843b017252d68162
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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