Water → 4-[(4-Ethynylphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

HRID 1716082Notes

Reaction equation

HRID 1716082 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][Si](C)(C)C)=[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+].O>CO>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:10](=[C:4]2[CH2:3][C:2]([CH3:30])([CH3:1])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5]2)[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:19][CH:20]=1)#[CH:25]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 686547694-((3,3,5,5-Tetramethylcyclohexylidene){4-[(trimethylsilyl)ethynyl]phenyl}methyl)phenol

Product 1

HCID 114052154-[(4-Ethynylphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenolYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-((3,3,5,5-Tetramethylcyclohexylidene){4-[(trimethylsilyl)ethynyl]phenyl}methyl)phenol (146) (0.175 g, 0.42 mmol) was dissolved in MeOH (10 mL). To this solution was added K2CO3 (0.18 g, 1.26 mmol). The reaction mixture was stirred at room temperature overnight, poured into water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic phase was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as brown solid. The crude product was purified by chromatography on a silica gel column eluted with a gradient from hexanes to 15% EtOAc:hexanes to give 0.14 g (97%) of the title compound 147 as white solid. mp 138-139° C. 1H NMR (400 MHz, CDCl3): δ 0.91 (s, 6H), 0.92 (s, 6H), 1.28 (s, 2H), 1.93 (s, 2H), 1.97 (s, 2H), 3.03 (s, 1H), 4.55 (br s, 1H), 6.73 (d, J=8.5 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 7.11 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.2 Hz, 2H). LCMS (ESI): m/z 343 (M−H)−.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give the crude product as brown solid
  7. customThe crude product was purified by chromatography on a silica gel column
  8. washeluted with a gradient from hexanes to 15% EtOAc

Sources & evidence

ORD record
ord-92ddbec592ea4c8b89e8c77980e9e556
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

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