3,4-dihydro-2H-pyran → HCID 22026143, compound

HRID 1793205Notes

Reaction equation

HRID 1793205 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([OH:10])=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([O:10][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10976084HCID 10976084, compound

Product 1

HCID 22026143HCID 22026143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2,5-Dihydroxy-3,4-dimethyl-phenyl)-ethanone of Step 3 (275 mg) was dissolved in dichloromethane (20 mL) and 3,4-dihydro-2H-pyran (0.2 mL) was added followed by pyridinium p-toluenesulfonate (PPTS) (30 mg). The mixture was stirred at room temperature for 4 h. The mixture was dried over MgSO4 and purified on silica gel column eluting with 30% EtOAc in hexane to give 397 mg of 1-[2-hydroxy-3,4-dimethyl-5-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone as a yellow solid.

Workup

  1. dry with materialThe mixture was dried over MgSO4
  2. custompurified on silica gel column
  3. washeluting with 30% EtOAc in hexane

Sources & evidence

ORD record
ord-0dedfd9308af4bb791ec2fa3e6564c11
Source dataset
uspto-grants-2006_07
Patent number
US07078541B2

Reaction notes

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