HCID 13066908, compound → HCID 13066910, compound

HRID 1074574Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18]I)[C:4]=1[CH3:20].O1CCCCC1[O:27][CH2:28][C:29]#[C:30][CH2:31][CH2:32][CH2:33][C:34]#[CH:35]>>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18][C:35]#[C:34][CH2:33][CH2:32][CH2:31][C:30]#[C:29][CH2:28][OH:27])[C:4]=1[CH3:20]

Participants

Reactant 2

HCID 13066908HCID 13066908, compound

HCID 13066909HCID 13066909, compound

Product 1

HCID 13066910HCID 13066910, compoundYield 73.5%

Procedure

By condensing 1,4-dimethoxy-2-methyl-3-(4-iodobutyl)naphthalene (3.84 g, 10 mmole) with 1-(2-tetrahydropyranyloxy)-2,7-octadiyne (2.10 g, 10 mmole) in accordance with the procedure of the above Reference Example 46, there was produced 1,4-dimethoxy-2-methyl-3-(12-hydroxy-5,10-dodecadiynyl)naphthalene (2.78 g, 73.5%, oily product). 1,4-Dimethoxy-2-methyl-3-(4-iodobutyl)naphthalene [δ1.5 to 2.2(4H), 2.40(3H), 2.82(2H), 3.23(2H), 3.84(3H), 3.87 (3H), 7.3 to 7.5(2H), 7.8 to 8.1(2H)] as utilized in this Reference Example was produced from 1,4-dimethoxy-2-methyl-3-(4-hydroxybutyl)naphthalene [oily substance, NMR (CDCl3), δ1.5 to 1.8(5H), 2.39(3H), 2.81(2H), 3.67(2H), 3.84(3H), 3.87(3H), 7.3 to 7.5(2H), 7.9 to 8.1(2H)] in accordance with the procedure described in Japanese Patent Application No. 49433/'80.

Sources & evidence

ORD record: ord-1f10ddd1d0e3467988f2007f30ded727
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04393075

Reaction notes

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