3,4-dihydro-2H-pyran → 8-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one

HRID 9259

Reaction equation

HRID 9259 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S([O-])(=O)=O)=[CH:9][CH:8]=1.[NH+]1C=C[CH:21]=[CH:20][CH:19]=1.[Cr](Cl)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[C:35]([O-])(=[O:37])C.[Na+]>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:37][CH2:35][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:17](=[O:25])[CH2:21][CH2:20][CH2:19]2

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 517045Sodium AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 219860898-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-oneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

The diol (Intermediate H3) (2.42 g, 13.5 mmol) was dissolved in CH2Cl2 (75 mL) and reacted with dihydropyran (1.3 mL, 13.8 mmol) and pyridinium para-toluene sulfonate (PPTS) (350 mg, 1.36 mmol) at rt for 18 h. The mixture was concentrated onto SiO2 and purified by chromatography with 10% EtOAc:Hx. The tetrahydropyranyl (THP) protected alcohol (2.02 g, 7.70 mmol) was dissolved in CH2Cl2 (10 mL) and added to a mixture of pyridinium chlorochromate (PCC) (4.9 g, 22.2 mmol), sodium acetate (310 mg, 3.56 mmol) and celite (˜10 g) in CH2Cl2 (100 mL). The mixture was reacted at rt for 18 h and filtered through celite. The residue was purified by chromatography on SiO2 with 20 to 30% EtOAc:Hx to yield 8-(tetrahydro-pyran-2-yloxymethyl)-3,4-dihydro-2H-naphthalen-1-one (Intermediate H4) (˜55%).

Workup

  1. concentrationThe mixture was concentrated onto SiO2
  2. custompurified by chromatography with 10% EtOAc
  3. customThe mixture was reacted at rt for 18 h
  4. filtrationfiltered through celite
  5. customThe residue was purified by chromatography on SiO2 with 20 to 30% EtOAc

Sources & evidence

ORD record
ord-c6bac18ad000457ea6e76f93c42ca587
Source dataset
uspto-grants-2006_08
Patent number
US07091232B2

Linked notes

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