Furfural → 1-(2-Furyl)but-3-yn-1-ol

HRID 1085314Notes

Reaction equation

HRID 1085314 reaction equation
[CH:1](=[O:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.O1C[CH2:11][CH2:10][CH2:9]1>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:7][CH:1]([C:2]1[O:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][C:10]#[CH:9]

Participants

6

Reactant 2

HCID 7362FurfuralHCID 8028Tetrahydrofuran

Product 1

HCID 109096231-(2-Furyl)but-3-yn-1-ol

Reagents, catalysts & solvents 3

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

Reaction and after-treatment were carried out in the same manner as in Example 18 except that an equimolar amount of furfural was used in place of 5-methylfurfural, and that cetyltrimethylammonium chloride and tetrahydrofuran were used in place of tetrabutylammonium bromide and toluene, respectively, in the same weights as those of the latter, to obtain 50.1 g of the fraction of 2-(1-hydroxy-3-butynyl)furan (content, 99.4%) (yield, 91.4%).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-d589804bbed34946b24e75fce160a8a6
Source dataset
uspto-grants-1991_04
Patent number
US05008410

Reaction notes

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