Potassium Carbonate → HCID 21100032, compound

HRID 1352203Notes

Reaction equation

HRID 1352203 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11]3)=[CH:4][CH:3]=1.Br[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH:20]1([CH2:19][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[C:10]4[C:14](=[CH:15][CH:16]=3)[C:13](=[O:17])[CH2:12][CH2:11]4)=[CH:6][CH:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 11206862HCID 11206862, compound

Product 1

HCID 21100032HCID 21100032, compoundYield 393.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-hydroxyphenyl)-1-indanone (0.52 g, 0.23 mmol, from Step A), bromomethylcyclohexane (0.53 g, 0.30 mmol) and potassium carbonate (0.58 g, 0.42 mmol) in acetonitrile (2.5 mL) was stirred at 80° C. for 16 h. The reaction mixture was cooled, diluted with ethyl acetate and washed with water. Silica gel chromatography eluting with 10% ethyl acetate/hexane yielded 0.29 g of product. 1H NMR (500 MHz, CDCl3): δ 7.83 (d, J=7.8 Hz, 1H), 7.67 (s, 1H), 7.60 (d, J=8.3 Hz, 3H), 7.03 (d, J=8.2 Hz, 2H), 3.85 (s, 2H), 3.21 (s, 2H), 2.78 (s, 2H), 2.08 (s, 1H), 1.90–1.98 (m, 2H), 1.80–1.86 (m, 2H), 1.20–1.42 (m, 4H), 1.07–1.18 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. washSilica gel chromatography eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d50014447c4d4ff9949d804060c74d79
Source dataset
uspto-grants-2007_05
Patent number
US07220734B2

Reaction notes

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