Vinyl Acetate → HCID 59557752, compound

HRID 2403773Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH:18]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:26](OC=C)(=O)[CH3:27]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][O:17][CH:26]=[CH2:27])=[CH:10][CH:9]=2)[CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-(4-(5-bromo-2-chlorobenzyl)phenyl)propan-1-ol (0.88 g, 2.59 mmol), [IrCl(cod)]2 (17 mg, 0.026 mmol) and sodium carbonate (0.17 g, 1.56 mmol) in toluene (5 mL) was added vinyl acetate (0.48 mL, 5.18 mmol) under argon. The reaction mixture was heated to 100° C. and stirred for 5 h. The solution was allowed to cool to room temperature, and then diluted with 60 mL of ethyl acetate. The mixture was washed with water (20 mL) and then with brine (20 mL), and dried over sodium sulfate. The residue was concentrated and purified by column chromatography (eluent EA:PE:Et3N=1:30:0.01) to provide 0.75 g of white solid. 1H NMR (CDCl3, 400 MHz): δ 7.29˜7.24 (m, 3H), 7.15 (d, 2H), 7.11 (d, 2H), 6.50 (dd, J=14.4 and 6.8 Hz, 1H), 4.18 (dd, J=14.4 and 2.0 Hz, 1H), 4.04 (s, 2H), 4.00 (dd, J=6.8 and 2.0 Hz, 1H), 3.71 (t, J=6.4 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 2.06˜1.96 (m, 2H).

Workup

temperatureto cool to room temperature
washThe mixture was washed with water (20 mL)
dry with materialwith brine (20 mL), and dried over sodium sulfate
concentrationThe residue was concentrated
custompurified by column chromatography (eluent EA:PE:Et3N=1:30:0.01)

Sources & evidence

ORD record: ord-578b9079379d47778d7ce101452bf371
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802637B2

Reaction notes

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