Tetrahydrofuran → HCID 59550253, compound

HRID 885768Notes

Reaction equation

HRID 885768 reaction equation
[OH:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][C:4]#[N:5].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.O1CCCC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCCCCC.O>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][C:4]#[N:5]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 15884599HCID 15884599, compound

Product 1

HCID 59550253HCID 59550253, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

2.16 g of (R)-3-hydroxy-tetradecanenitrile, 1.93 ml of dihydropyran and 20 ml of tetrahydrofuran were placed in a reactor and stirred, and 266 mg of pyridinium p-toluenesulfonate was added thereto, heated to 50° C., and stirred for about 2 hours. The mixture was cooled to room temperature, 30 ml of water and 30 ml of hexane were added thereto, and stirred vigorously for 5 minutes. The resulting mixture was allowed to undergo phase separation and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure, to give 2.97 g of the title compound (yield: 100%) as an oil.

Workup

  1. stirringstirred for about 2 hours
  2. temperatureThe mixture was cooled to room temperature
  3. stirringstirred vigorously for 5 minutes
  4. customphase separation
  5. customthe aqueous layer was removed
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-2fc371b528304a6cbd7b0dbe83ad8fae
Source dataset
uspto-grants-2012_08
Patent number
US08242288B2

Reaction notes

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