Triethylamine → HCID 15107376, compound

HRID 2108236Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]=1)(=[O:28])=[O:27]

Participants

Conditions

Temperature: 3 °C

Procedure

To 5.03 g (0.0216 mole) of 2-(2-hydroxyethyl)-6,7dimethoxynaphthalene in 75 mL of methylene chloride, cooled in an ice bath, was added 6 mL (0.043 mole) of triethylamine followed by 2.2 mL (0.028 mole) of methanesulfonyl chloride. The reaction mixture was stirred at 3° C. for 1 hour and then was washed with 1N hydrochloric acid, 5% sodium bicarbonate solution. The organic layer was dried and concentrated under reduced pressure to give 2-(2-methanesulfonyloxyethyl)-6,7-dimethoxynaphthalene, which was used without purification. A mixture of this mesylate, 5.5 g (0.019 mole) of 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester, 0.7 mL of TDA-1 and 5.4 g (0.039 mole) of potassium carbonate in 180 mL of toluene was stirred at reflux for 18 hours. The reaction mixture was washed with water, dried and concentrated under reduced pressure to a solid which was recrystallized from methylene chloride-methanol-water, to give 8.6g (89% yield), mp 112°-113° C., of 2-hydroxy-4-[2-(6,7-dimethoxy-2-naphthalenyl)ethoxy]-3-propylbenzoic acid phenylmethyl ester.

Workup

washwas washed with 1N hydrochloric acid, 5% sodium bicarbonate solution
customThe organic layer was dried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-bce603acf1ef445b801ad6c650806067
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04937371

Reaction notes

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