Trityl chloride → 4-[2-(Trityloxy)ethyl]cyclohexanol

HRID 45014Notes

Reaction equation

HRID 45014 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1.[C:11]1([C:17](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:17]([O:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 137511534-(2-Hydroxyethyl)cyclohexan-1-ol

Product 1

HCID 574779704-[2-(Trityloxy)ethyl]cyclohexanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-Hydroxyethyl)cyclohexanol (crude from the previous reaction) (1.88 g, 0.0130 mol) was dissolved in pyridine (20.00 mL) and was cooled at 0° C. To the reaction was added triphenylmethyl chloride (4.0 g, 0.014 mol) and this mixture was stirred at 0° C. for 2 hours and at 25° C. for 16 hours. The reaction was concentrated using a rotary evaporator and the concentrate was extracted with ethyl acetate. The organic extracts were washed with water, and saturated NaCl, then dried (MgSO4) and concentrated in vacuo. The concentrate was chromatographed on silica gel (30% EtOAc/hexanes) to give the trans isomer (1.98 g)

Workup

  1. concentrationThe reaction was concentrated
  2. customa rotary evaporator
  3. extractionthe concentrate was extracted with ethyl acetate
  4. washThe organic extracts were washed with water, and saturated NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe concentrate was chromatographed on silica gel (30% EtOAc/hexanes)
  8. customto give the trans isomer (1.98 g)

Sources & evidence

ORD record
ord-62ef1f5595e049c9850be51620c9a217
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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