Dicyclohexylcarbodiimide → Pentafluorphenyl 6-octyloxy-2-naphthoate

HRID 2292821Notes

Reaction equation

[CH2:1]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([OH:22])=[O:21])[CH:14]=[CH:13]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(N=C=NC2CCCCC2)CCCCC1.[F:38][C:39]1[C:44](O)=[C:43]([F:46])[C:42]([F:47])=[C:41]([F:48])[C:40]=1[F:49]>C(OCC)(=O)C>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([O:22][C:44]1[C:43]([F:46])=[C:42]([F:47])[C:41]([F:48])=[C:40]([F:49])[C:39]=1[F:38])=[O:21])[CH:14]=[CH:13]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 6-octyloxy-2-naphthoic acid (3.15 g, 10.5 mmol) and dicyclohexylcarbodiimide in ethyl acetate (25 ml) at 0° C. was added pentafluorophenol (2.12 g, 11.5 mmol). The mixture was stirred at 25° C. for a period of 18 h. The precipitate was removed by filtration. The filtrate was washed with water (2×150 ml) and brine and dried with magnesium sulfate. Removal of the ethyl acetate in vacuo gave 5.4 g of pentafluorphenyl 6-octyloxy-2-naphthoate as a solid: 1 H NMR (400 MHz, CD3OD) δ0.88 (t, 3H, J =6.9 Hz), 4.10 (t, 2H, J=6.6 Hz), 7.16 (d, 1H), 7.21 (d, 1H), 7.80 (d, 1H), 7.87 (d, 1H), 8.08 (dd, 1H), 8.69 (d, 1H).

Workup

customThe precipitate was removed by filtration
washThe filtrate was washed with water (2×150 ml) and brine
dry with materialdried with magnesium sulfate
customRemoval of the ethyl acetate in vacuo

Sources & evidence

ORD record: ord-ccdde320cec849cc9b708125f03dfb81
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05684128

Reaction notes

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