1,4-Cyclohexanediol → HCID 69201041, compound

HRID 2252265Notes

Reaction equation

HRID 2252265 reaction equation
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[CH3:11][Si:12]([CH2:15][CH2:16][O:17][CH2:18]Cl)([CH3:14])[CH3:13]>C1COCC1>[CH3:11][Si:12]([CH3:14])([CH3:13])[CH2:15][CH2:16][O:17][CH2:18][O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 111621,4-CyclohexanediolHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 69201041HCID 69201041, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexane-1,4-diol (4 g, 34.8 mmol) was dissolved in THF (200 mL). To this solution was added 95% NaH (0.922 g, 36.6 mmol). The mixture was heated to reflux for 1 hour. Then 10 the reaction was cooled down. SEMCl (6.44 mL, 36.6 mmol) was added dropwise. The reaction mixture was heated to reflux again overnight. THF was removed. The residue was purified by flash chromatography to give the desired product (2.10 g, 16%). MS (DCI/NH3) m/z 247 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.02 (s, 9H) 0.87-0.95 (m, 2H) 1.30-1.38 (m, 2H) 1.57 (m, 1H) 1.64-1.70 (m, 2H) 1.80 (m, 1H) 1.91-2.01 (m, 2H) 3.50-3.70 (m, 4H) 4.69 (s, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThen 10 the reaction was cooled down
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux again overnight
  6. customTHF was removed
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6b1d9be224bd4b158beecf34ac621ae9
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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