Cyanic acid → Tetrahydropyranyl ether

HRID 64921

Reaction equation

HRID 64921 reaction equation
[C:1]([OH:3])#N.[O:4]1[CH:9]=[CH:8][CH2:7][CH2:6][CH2:5]1.[C:10]1(C)C=C[C:13](S(O)(=O)=O)=[CH:12][CH:11]=1.CC[O:23]CC>C(Cl)Cl>[O:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[O:23][CH:13]1[CH2:12][CH2:11][CH2:10][CH2:1][O:3]1

Participants

6

Reactant 4

HCID 540Cyanic acidHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 263182Tetrahydropyranyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.23 g of Part F cyano-alcohol (7.36 mmole) in 20 ml of dry methylene chloride was treated with 800 ml of dihydropyran (8.89 mmole) and catalytic amount of p-toluene sulfonic acid at 0°-5° C. After 4 hours, the reaction mixture was diluted with ether and washed with aqueous sodium bicarbonate solution. The aqueous layer was reextracted twice with ether. The combined organic extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude residue was chromatographed on a silica gel column and eluted with 2 ethyl acetate in hexane to obtain 1.61 g of title tetrahydropyranyl ether.

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. extractionThe combined organic extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was chromatographed on a silica gel column
  6. washeluted with 2 ethyl acetate in hexane

Sources & evidence

ORD record
ord-fb020a548ac8493380d7e8595f454fac
Source dataset
uspto-grants-1986_09
Patent number
US04611005

Linked notes

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