3,4-dihydro-2H-pyran → HCID 57121539, compound

HRID 1873097Notes

Reaction equation

HRID 1873097 reaction equation
[CH3:1][C:2]1[CH2:3][C@H:4]([OH:11])[CH2:5][C:6]([CH3:10])([CH3:9])[C:7]=1[CH3:8].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[O:11][C@@H:4]1[CH2:5][C:6]([CH3:10])([CH3:9])[C:7]([CH3:8])=[C:2]([CH3:1])[CH2:3]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 57184026HCID 57184026, compound

Product 1

HCID 57121539HCID 57121539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.8 g (5.2 mmol) of (1S)-3,4,5,5-tetramethyl-3-cyclohexen-1-ol prepared in Example 2A was dissolved in 5 ml of absolute methylene chloride under N2, the solution was cooled to 0° C., and then firstly 260 mg (1.04 mmol) of pyridinium p-toluenesulfonate and then 450 mg (6.2 mmol) of 3,4-dihydropyran were added. The mixture was subsequently stirred at 0° C. for 1 h and then poured into saturated NaHCO3 solution and extracted with methylene chloride. The extract was dried over MgSO4 and concentrated to result in 1.1 g (corresponding to 89% of theory) of the desired product.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ee1c722f695348569e25a2ac9ce7660c
Source dataset
uspto-grants-2000_08
Patent number
US06111125

Reaction notes

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