3,4-dihydro-2H-pyran → HCID 14405876, compound

HRID 1198039Notes

Reaction equation

HRID 1198039 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C([O-])(O)=O.[Na+]>C1COCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 7903412-Hydroxydodecanoic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 14405876HCID 14405876, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12-hydroxydodecanoic acid (10.0 g, 0.046 mol) in 150 mL THF, p-toluenesulfonic acid (0.087 g, 0.01 eq) was added followed by 3,4-dihydro-2H-pyran (5.95 g, 0.070 mol). After stirring this homogeneous reaction mixture for 16 hours at room temperature under a nitrogen atmosphere, NaHCO3 saturated solution was added to the mixture. The mixture was then extracted with methylene chloride, dried (MgSO4), and concentrated in vacuo (30° C.) to yield 13.0 g (0.043 mol, 94%) of the desired product.

Workup

  1. extractionThe mixture was then extracted with methylene chloride
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo (30° C.)

Sources & evidence

ORD record
ord-045cb18ec97b4c76a055ecf7b25a2ee6
Source dataset
uspto-grants-1994_01
Patent number
US05278326

Reaction notes

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