Ethyl bromoacetate → [6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

HRID 1359251Notes

Reaction equation

HRID 1359251 reaction equation
[CH2:1]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]=1[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([OH:25])[CH:19]=[CH:18]2)[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CC(C)=O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][O:25][C:20]1[CH:19]=[CH:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([C:7]3[O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:6]=3[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:16]=2)[CH:21]=1)[CH3:38]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 181827756-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-ol

Product 1

HCID 69830661[6-(3-Pentyl-benzofuran-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl esterYield 93.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following the procedure described in Method B, Step 5 of Example 1, the title compound was prepared from 6-(3-pentyl-benzofuran-2-yl)-naphthalen-2-ol (0.33 g, 1 mmol), cesium carbonate (0.75 g, 2.3 mmol), ethyl bromoacetate (0.16 mL, 1.4 mmol) in acetone (20 mL). Crystallization from hexane furnished the title compound as a white solid (0.39 g), mp 84-86° C. Mass spectrum (+APCl, [M+H]+) m/z 417. 1HNMR (300 MHz, DMSO-d6): δ8.25 (s, 1H), 8.00 (d, 1H, J=9.1 Hz), 7.94-7.84 (m, 2H), 7.69-7.66 (m, 1H), 7.60 (d, 1H, J=7.5 Hz), 7.35-7.25 (m, 4H), 4.93 (s, 2H), 4.20 (q, 2H, J=7.1 Hz), 2.98 (t, 2H, J=7.3 Hz), 1.72 (p, 2H, J=7.3 Hz), 1.43-1.28 (m, 4H), 1.23 (t, 3H, J=7.2 Hz), and 0.83 ppm (t, 3H, J=7.1 Hz). Elemental Analysis for C27H28O4.0.5H2O: Calculated: C, 76.21; H, 6.87; N, 0.00. Found: C, 76.48; H, 6.69; N, 0.12.

Workup

  1. customCrystallization from hexane

Sources & evidence

ORD record
ord-f66630090a1e4052bca271aca4de6fe9
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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