3,4-dihydro-2H-pyran → 1-Heptadecene

HRID 378199Notes

Reaction equation

HRID 378199 reaction equation
C([C:4]12[CH2:18][CH:15]([CH2:16][CH2:17]1)[CH:14]1[C:5]2=[C:6]2[CH2:19][CH:13]1[CH:12]1[CH:7]2[CH:8]2[CH2:20][CH:11]1[CH2:10][CH2:9]2)(O)=O.O1C=CCCC1>O1CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC>[CH2:16]=[CH:17][CH2:4][CH2:18][CH2:15][CH2:14][CH2:5][CH2:6][CH2:19][CH2:13][CH2:12][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:20]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 86755175Carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecen

Product 1

HCID 232171-Heptadecene

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6101p-Toluenesulfonic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Subsequently, carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14 ]heptadecen of 2.1 grams and 3,4-dihydro-2H-pyran of 1.71 grams were dissolved in tetrahydrofuran of 50 milli-litter, and p-toluen sulfonic acid of 0.03 gram was added to the solution. The reaction was continued at room temperature for 2 hours. The resultant material was diluted in ether of 100 milli-litter, and was washed in 3% solution of Na2CO3, saturated water of salt and water in this order, and the organic layer was dried with MgSO4. When ether and residual 3,4-dihydro-2H-pyran were removed in vacuum by using an evaporator, we obtained viscous-liquid of 12-tetrahydropyranyloxycarbonilhexacyclo[6.6.1.13,6.110,13.02,7.09,14 ]heptadecen of 2 grams.

Workup

  1. additionwas added to the solution
  2. washwas washed in 3% solution of Na2CO3, saturated water of salt and water in this order
  3. dry with materialthe organic layer was dried with MgSO4
  4. customWhen ether and residual 3,4-dihydro-2H-pyran were removed in vacuum
  5. customan evaporator, we

Sources & evidence

ORD record
ord-b097b090a3c541ebbc2a013b8f37936f
Source dataset
uspto-grants-2000_02
Patent number
US06030747

Reaction notes

Loading…