Potassium Carbonate → 3-(4-[2-(2,10-Dichloro-12H-5,7-dioxa-dibenzo[a,d]cycloocten-1 2-yloxy)-ethoxy]-phenyl)-2-ethoxy-propionic acid ethyl ester

HRID 323592Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][CH:5]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[O:10][CH2:9][O:8][C:7]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:6]1=2.[CH2:23]([O:25][C:26](=[O:39])[CH:27]([O:36][CH2:37][CH3:38])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[CH2:23]([O:25][C:26](=[O:39])[CH:27]([O:36][CH2:37][CH3:38])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH2:2][CH2:3][O:4][CH:5]2[C:12]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=3[O:10][CH2:9][O:8][C:7]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:6]2=3)=[CH:33][CH:34]=1)[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 12-(2-bromo-ethoxy)-2,10-dichloro-12H-5,7-dioxa-dibenzo[a,d]cyclooctene (404 mg, 1.0 mmol) and 2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (238 mg, 1.0 mmol) in dry toluene (6 mL) was added potassium carbonate (276 mg, 2.0 mmol) and 18-crown-6 (528 mg, 2.0 mmol). The mixture was heated at 60° C. for 16 h. The mixture was filtered, and concentrated in vacuo. The residue was submitted to flash chromatography using toluene/ethyl acetate (19:1) as eluent to give 297 mg (53%) of the title compound; 1H NMR (300 MHz, CDCl3) δ1.18 (t, 3H), 1.25 (t, 3H), 2.96 (d, 2H), 3.30-3.42 (m, 1H), 3.55-3.65 (m, 1H), 3.90-3.95 (m, 2H), 4.0 (t, 1H), 4.15-4.25 (m, 4H), 4.55 (d, 1H), 5.87)d, 1H), 6.18 (s, 1H), 6.88-6.95 (m, 4H), 7.10-7.25 (m, 4H), 7.60 (d, 2H).

Workup

filtrationThe mixture was filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-46acc6604b09459dae121ad7634b741e
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06214820B1

Reaction notes

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