5-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione → Ethyl 3-(4-hydroxyphenyl)hex-4-ynoate

HRID 1160281Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]2C(=O)O[C:15](C)([CH3:19])[O:14][C:13]2=[O:21])[C:9]#[C:10][CH3:11])=[CH:4][CH:3]=1>N1C=CC=CC=1.C(O)C>[CH2:15]([O:14][C:13](=[O:21])[CH2:12][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[C:9]#[C:10][CH3:11])[CH3:19]

Participants

Conditions

Temperature: 90 °C

Procedure

Phenol 1.2 (1.2 g, 4 mmol) was dissolved in pyridine (3 mL) and ethanol (1 mL). The mixture was heated to 90° C. for 16 h and then concentrated to an oil which was purified by column chromatography (elution with 1-3% MeOH in dichloromethane). Phenol 16 (0.88 g, 91%) was obtained as an oil. 1H NMR(500 MHz)(acetone-d6) δ 8.24 (s, 1H); 7.21 (d, 2H, J=9.5 Hz); 6.78 (d, 2H, J=9.0 Hz); 4.06 (m, 2H); 3.98 (m, 1H); 2.68-2.59 (m, 2H); 1.78 (d, 3H, J=2.5 Hz); 1.75 (t, 3H, J=7.0 Hz). MS ESI (pos.) m/e: 233.1 (M+H); 255.1 (M+Na).

Workup

concentrationconcentrated to an oil which
customwas purified by column chromatography (elution with 1-3% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-a5b987b8b2d34536bb89d49471258f62
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816367B2

Reaction notes

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