3,4-dihydro-2H-pyran → HCID 15476080, compound

HRID 2289367Notes

Reaction equation

HRID 2289367 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:26])[CH:12]=[CH:11][C:10]([S:13]([O:16][CH2:17][C@H:18]([OH:25])[CH2:19][CH2:20][C@@H:21]([CH3:24])[CH2:22][CH3:23])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>[C:7]1([CH3:26])[CH:8]=[CH:9][C:10]([S:13]([O:16][CH2:17][C@H:18]([O:25][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)[CH2:19][CH2:20][C@@H:21]([CH3:24])[CH2:22][CH3:23])(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 15476078HCID 15476078, compound

Product 1

HCID 15476080HCID 15476080, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

In a 50 ml egg-plant type flask were charged 1.7 g of 3,4-dihydro-2H-pyran, 30 ml of diethyl ether, 5.0 g of (2R,5S)-2-hydroxy-5-methylheptyl p-toluenesulfonate, and 50 mg of p-toluenesulfonic acid, and the mixture was stirred at room temperature overnight. The resulting reaction mixture was neutralized with a saturated sodium hydrogencarbonate aqueous solution, and diethyl ether was distilled off under reduced pressure to obtain 6.5 g of a crude product.

Workup

  1. customThe resulting reaction mixture
  2. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-7ee85f00da834922acb47612ebc3ff6e
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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