Toluene → HCID 86704384, compound

HRID 1476365Notes

Reaction equation

HRID 1476365 reaction equation
C#CCC.[CH2:5]([C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([O:25][CH3:26])=[CH:22]2)=[CH:17][CH:16]=1)[CH2:6][CH2:7][CH2:8]CCCCCC.C1(C)C=CC=CC=1>CCCCCC>[C:5]([C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([O:25][CH3:26])=[CH:22]2)=[CH:17][CH:16]=1)#[C:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78461-ButyneHCID 86704382HCID 86704382, compound

Product 1

HCID 86704384HCID 86704384, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using 7-methoxy-2-naphthyltrifluoromethanesulfonate (30.63 g, 0.10 mol) and butyne gas (a product manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD., 100 g, large excess), 7-butyn-1-yl-2-methoxynaphthalene was synthesized by the same operation as that in the method for synthesizing 7-decyl-2-methoxynaphthalene according to Example 3, and subjected to column chromatography (silica gel, developed with a mixture of toluene and hexane) to obtain a light yellow oil product of 7-butyn-1-yl-2-methoxynaphthalene (18.1 g, yield of 56%). The obtained 7-butyn-1-yl-2-methoxynaphthalene (total amount) was subjected to catalytic reduction in toluene (275 ml) under a hydrogen atmosphere by adding 10% Pd/C (1.83 g). The obtained product was subjected to column chromatography (silica gel, developed with a mixture of toluene and hexane) to obtain 7-butyl-2-methoxynaphthalene (compound (3)-04, 17.80 g, yield of 97%).

Workup

  1. custom, 100 g, large excess), 7-butyn-1-yl-2-methoxynaphthalene was synthesized by the same operation as that in the method

Sources & evidence

ORD record
ord-daba7c0b70bf44119fda4bca2b4de546
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

Loading…