Triethylamine → HCID 57617606, compound

HRID 1960040Notes

Reaction equation

HRID 1960040 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15]C(=O)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(O)C>[CH2:26]([O:25][C:21]1([O:22][CH2:23][CH3:24])[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:16][CH2:15]1)[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 218796054-(2-Benzyloxyethyl)cyclohexanone

Product 1

HCID 57617606HCID 57617606, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-benzyloxyethyl)cyclohexanone (133.0 g, 0.57 mol) is dissolved in ethanol (1200 mL), and then triethylorthoformate (296 mL) and p-toluenesulfonic acid monohydrate (10.9 g, 0.057 mol) are added. The resulting mixture is stirred and refluxed for 2 hours. After addition of triethylamine (8.8 mL, 0.063 mol) at room temperature, the mixture is concentrated. After addition of sat. NaHCO3 aq. (500 mL), the resulting mixture is extracted with EtOAc (1000 mL). The water layer is extracted with EtOAc (1000 mL×2) and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude mixture is purified by short pad silica gel column chromatography to afford [2-(4,4-diethoxycyclohexyl)ethoxymethyl]benzene as a pale yellow oil.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationthe mixture is concentrated
  3. additionAfter addition of sat. NaHCO3 aq. (500 mL)
  4. extractionthe resulting mixture is extracted with EtOAc (1000 mL)
  5. extractionThe water layer is extracted with EtOAc (1000 mL×2)
  6. washthe combined organic layer is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude mixture is purified by short pad silica gel column chromatography

Sources & evidence

ORD record
ord-edac36e6e0b04410bbe75966019b862e
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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