Potassium Carbonate → HCID 44528944, compound

HRID 1716138Notes

Reaction equation

HRID 1716138 reaction equation
N1C=CC=C1[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[C:20]2[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.C([O-])([O-])=[O:31].[K+].[K+].Br[C:37]([CH3:44])([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39]>CC(C)=O>[OH:31][C:6]1[CH:7]=[CH:8][C:9]([C:12](=[C:20]2[CH2:25][C:24]([CH3:26])([CH3:27])[CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)[C:13]2[CH:14]=[CH:15][C:16]([O:19][C:37]([CH3:44])([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:17][CH:18]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 11395037HCID 11395037, compound

Product 1

HCID 44528944HCID 44528944, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The O-alkylation procedure described for 190 was employed. To a suspension of 4,4′-[(3,3,5,5-tetramethylcyclohexylidene)methanediyl]diphenol (19) (0.500 g, 1.74 mmol), K2CO3 (0.257 g, 1.86 mmol), and acetone (75 mL) was added ethyl 2-bromo-2-methylpropanoate (0.33 mL, 2.3 mmol) at RT. The reaction mixture was refluxed for 48 h, and filtered. The filtrate was concentrated and purified to afford 0.272 g (40%) of compound 227 as a white foam. In addition, 0.200 g of unreacted SM was recovered. 1H NMR (300 MHz, CDCl3): δ7.04 (d, J=1.8 Hz, 2H), 7.01 (d, J=1.8 Hz, 2H), 6.76 (d, J=1.5 Hz, 2H), 6.77 (d, J=2.7 Hz, 2H), 6.74 (d, J=2.4 Hz, 2H), 4.75 (br s, 1H), 4.24 (q, J=7.2 Hz, 2H), 1.96 (d, J=6.9 Hz, 4H), 1.60 (s, 6H), 1.29 (s, 2H), 1.23 (t, J=7.2 Hz, 3H), 0.934 (s, 6H), 0.92 (s, 6H). LCMS (ESI): m/z 449 (M−H)−.

Workup

  1. temperatureThe reaction mixture was refluxed for 48 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-74c00114962a4cfa846f1411a4d6eb7c
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

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