p-Toluenesulfonic acid → HCID 178495006, compound

HRID 2404151Notes

Reaction equation

HRID 2404151 reaction equation
[CH3:1][O:2][C:3]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12]C2CCCCO2)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3]([C@H:6]1[CH2:7][CH2:8][C@H:9]([OH:12])[CH2:10][CH2:11]1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178495005HCID 178495005, compound

Product 1

HCID 178495006HCID 178495006, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-((trans)-4-(2-methoxypropan-2-yl)cyclohexyloxy)tetrahydro-2H-pyran (1.2 g, 4.7 mmol) in MeOH (10 mL) was added p-TsOH (8.9 g, 4.7 mmol, 1.0 eq) slowly at rt. Then the mixture was stirred at rt for 2 h, and the solvent was removed in vacuo. The residue was purified on silica gel (EA/PE=1:3) to give the title compound as a colorless oil (660 mg, yield: 82%). 1H NMR (400 MHz, CDCl3) δ: 4.07-4.05 (m, 1H), 3.17 (s, 3H), 1.87-1.82 (m, 2H), 1.55-1.38 (m, 7H), 1.10 (s, 6H).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified on silica gel (EA/PE=1:3)

Sources & evidence

ORD record
ord-d143c145fe3f4aa391c1d89f7aa98787
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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