반응 #705261

반응 방정식

3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone

ethylene glycol

p-toluenesulfonic acid monohydrate

3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

Compound 100C

3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

Compound 100D

3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone

→

title compound

4-[(5,6-dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoic acid

용매

benzene

반응 조건

후처리

1. 1
   온도The resulting solution was heated
2. 2
   온도to reflux for 18 hours
3. 3
   농축concentrated under reduced pressure

실험 절차

A solution of 1.80 g (8.34 mmol) of a 1:5 mixture of 3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone (Compound 100C); and 3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone (Compound 100D) in 50 ml benzene was combined with 517.7 mg (8.34 mmol) of ethylene glycol and 20.0 mg (0.11 mmol) of p-toluenesulfonic acid monohydrate. The resulting solution was heated to reflux for 18 hours, cooled to room temperature, and concentrated under reduced pressure. The title compound was isolated by column chromatography (10% EtOAc-hexanes) as a colorless oil. 1H NMR (CDCl3): δ 8.01 (1H, d, J=8.2 Hz), 7.51 (1H, s), 7.43 (1H, dd, J=1.7, 6.4 Hz), 4.07 (2H, m), 3.79 (2H, m), 2.74 (2H, t, J=6.5 Hz), 2.04 (2H, t, J=7.1 Hz), 1.67 (3H, s), 1.46 (6H, s).

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