Hexane → HCID 90473388, compound

HRID 1476366Notes

Reaction equation

HRID 1476366 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([O:15][CH3:16])=[CH:12]2)=[CH:7][CH:6]=1)#[C:2][CH2:3][CH3:4].CCCCCC>C1(C)C=CC=CC=1.[Pd]>[CH2:1]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([O:15][CH3:16])=[CH:12]2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8058HexaneHCID 86704384HCID 86704384, compound

Product 1

HCID 90473388HCID 90473388, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

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%).

Sources & evidence

ORD record
ord-b357500ecfec49618b196bc321af03e3
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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