4-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran → 4-(tetrahydro-2H-pyran-4-yloxy)phenol

HRID 513183Notes

Reaction equation

HRID 513183 reaction equation
C([O:5][C:6]1[CH:18]=[CH:17][C:9]([O:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:8][CH:7]=1)(C)(C)C>C(O)(C(F)(F)F)=O>[O:14]1[CH2:13][CH2:12][CH:11]([O:10][C:9]2[CH:17]=[CH:18][C:6]([OH:5])=[CH:7][CH:8]=2)[CH2:16][CH2:15]1

Participants

3

Reactant 1

HCID 712121564-(4-tert-butoxyphenoxy)tetrahydro-2H-pyran

Product 1

HCID 639360494-(tetrahydro-2H-pyran-4-yloxy)phenolYield 94.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(4-Tert-butoxyphenoxy)tetrahydro-2H-pyran (257 mg, 1.027 mmole) was taken up in TFA (5 mL) at RT. After 90 min the mixture was concentrated. The residue was taken up in saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the title compound (188 mg, 94%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 6.82 (m, 2 H); 6.77-6.73 (m, 2 H); 4.71 (s, 1 H); 4.37-4.29 (m, 1 H); 4.03-3.95 (m, 2 H); 3.55 (m, 2 H); 2.03-1.95 (m, 2 H); 1.81-1.70 (m, 2 H).

Workup

  1. concentrationAfter 90 min the mixture was concentrated
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bbf051b96b994ea897249641ab6b6130
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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