Potassium Carbonate → HCID 11992776, compound

HRID 2241060Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-(2-chloroethoxy)ethanol (139 mg, 1.12 mmol), compound 41 (150 mg, 0.45 mmol), and K2CO3 (185 mg, 1.34 mmol) were combined with dry acetone (5 mL) in a sealed microwave vessel. The mixture was heated at 100° C. for 20 minutes in a Personal Chemistry Emrys Optimizer microwave. The reaction was allowed to cool to room temperature and the solids were removed via filtration. The solids were rinsed twice with acetone and the solvent was removed in vacuuo. The reaction was purified using the Agilent semi prep HPLC (LUNA C18 column, 23 mL/min, 30-70% CH3CN-Water (TFA) to give 76 mg (40%) of the desired compound 50 as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.91 (s, 6H), 0.93 (s, 6H), 1.23 (s, 2H), 1.95 (s, 2H), 1.96 (s, 2H), 2.13 (s, 3H), 3.7-3.78 (m, 2H), 3.87 (t, J=4.6 Hz, 2H), 4.1 (t, J=4.8 Hz, 2H), 6.72 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.6 Hz, 2H), 7.10-7.20 (m, 3H), 7.20-7.30 (m, 2H).

Workup

temperatureto cool to room temperature
customthe solids were removed via filtration
washThe solids were rinsed twice with acetone
customthe solvent was removed in vacuuo
customThe reaction was purified

Sources & evidence

ORD record: ord-0666015298a9453d8f7f7ad0bd5eef77
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723393B2

Reaction notes

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