3,4-dihydro-2H-pyran → HCID 86583769, compound

HRID 411880Notes

Reaction equation

HRID 411880 reaction equation
[C:1]([CH:4]1[CH:17]2[CH2:18][CH:6]([CH:7]3[CH:16]2[C:15]2[CH2:19][CH:8]3[CH:9]3[C:14]=2[CH:13]2[CH2:20][CH:10]3[CH2:11][CH2:12]2)[CH2:5]1)([OH:3])=[O:2].[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1>O1CCCC1.C(OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:2][C:1]([CH:4]1[CH:17]2[CH2:18][CH:6]([CH:7]3[CH:16]2[C:15]2[CH2:19][CH:8]3[CH:9]3[C:14]=2[CH:13]2[CH2:20][CH:10]3[CH2:11][CH2:12]2)[CH2:5]1)=[O:3]

Participants

6

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 86583767HCID 86583767, compound

Product 1

HCID 86583769HCID 86583769, compoundYield 72.6%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Next, 2.1 g of the 12-carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene and 1.71 g of 3,4-dihydro-2H-pyran were dissolved in 50 ml of tetrahydrofuran, into which 0.03 g of p-toluenesulfonic acid were added. The resultant mixture was reacted at room temperature for 2 hours. The reaction mixture was diluted with 100 ml of ethyl ether, followed by the successive washing with a 3% aqueous solution of Na2CO3, 3% aqueous solution of sodium chloride, and water. An organic layer was dried over MgSO4. The ethyl ether and unreacted 3,4-dihydro-2H-pyran were distilled off under reduced pressure by an evaporator, whereby 2 g of 12-tetrahydropyranyloxycarbonylhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene were obtained as a viscous liquid.

Workup

  1. additionwere added
  2. washsuccessive washing with a 3% aqueous solution of Na2CO3, 3% aqueous solution of sodium chloride, and water
  3. dry with materialAn organic layer was dried over MgSO4
  4. distillationThe ethyl ether and unreacted 3,4-dihydro-2H-pyran were distilled off under reduced pressure by an evaporator

Sources & evidence

ORD record
ord-b619af84a3904d76a1fcf1418226f13f
Source dataset
uspto-grants-2003_05
Patent number
US06559337B2

Reaction notes

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