3,4-dihydro-2H-pyran → HCID 57144221, compound

HRID 2289377Notes

Reaction equation

HRID 2289377 reaction equation
[OH:1][C@@H:2]([C@@H:8]([CH3:11])[CH2:9][CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])O.[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][C@@H:2]([C@@H:8]([CH3:11])[CH2:9][CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 13026601HCID 13026601, compound

Product 1

HCID 57144221HCID 57144221, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

In a 200 ml flask were charged 10 g of ethyl (2S,3S)-2-hydroxy-3-methylvalerate, 10.5 g of 3,4-dihydro-2H-pyran, 0.24 g of p-toluenesulfonic acid, and 100 ml of diethyl ether, and the mixture was allowed to react at room temperature overnight. The reaction mixture was neutralized with a sodium hydrogencarbonate aqueous solution, and diethyl ether was removed by distillation to obtain 6.15 g (49.7%) of a crude product.

Workup

  1. customto react at room temperature overnight
  2. customwas removed by distillation

Sources & evidence

ORD record
ord-0b84ad6928594ed6875924772acc3d90
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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