Acetic Acid → 5-(4-{4-[2-(4-Methoxyphenyl)-vinyl]-phenoxy}-benzyl)-thiazolidine-2,4-dione

HRID 2238269

Reaction equation

HRID 2238269 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1.[CH3:30]C(C)([O-])C.[K+].[O:36]=[C:37]1[NH:41][C:40](=[O:42])[CH:39]([CH2:43][C:44]2[CH:58]=[CH:57][C:47]([O:48][C:49]3[CH:56]=[CH:55][C:52](C=O)=[CH:51][CH:50]=3)=[CH:46][CH:45]=2)[S:38]1.C(O)(=O)C>C1COCC1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:30][C:52]2[CH:55]=[CH:56][C:49]([O:48][C:47]3[CH:57]=[CH:58][C:44]([CH2:43][CH:39]4[S:38][C:37](=[O:36])[NH:41][C:40]4=[O:42])=[CH:45][CH:46]=3)=[CH:50][CH:51]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2773651(4-Methoxybenzyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 597682934-[4-(2,4-Dioxothiazolidin-5-ylmethyl)-phenoxy]-benzaldehyde

Product 1

HCID 865896865-(4-{4-[2-(4-Methoxyphenyl)-vinyl]-phenoxy}-benzyl)-thiazolidine-2,4-dioneYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-methoxybenzyltriphenylphosphonium chloride (419 mg, 1.0 mmol) in THF (10 mL) at 0° C. was added solid potassium tert-butoxide (224 mg, 2.0 mmol). The resultant orange-red solution was stirred for 15 min at 0° C. then cooled to −45° C. Solid compound 53 (327 mg, 1.0 mmol) was added and the reaction mixture stirred for 30 min at this temperature. To this pale yellow solution glacial acetic acid (60 μL, 1 mmol) was added and the solvent was removed in vacuo. The crude product was suspended in dichloromethane, adsorbed onto silica gel and purified by flash chromatography using hexanes-ethyl acetate (7:3) to yield a white solid (143 mg, 33%) after drying under high vacuum. 1H NMR: (400 MHz, DMSO-d6): δ 12.04 (bs, 1H), 7.27 (d, J=8.0 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 6.97 (d, J=8.4 Hz, 2H), 6.88 (d, J=8.8 Hz, 2H), 6.84 (d, J=8.8 Hz, 2H), 6.53 (d, J=12.4 Hz, 2H), 6.48 (d, J=12.0 Hz, 2H), 4.90 (dd, J=9.2 and 4.4 Hz, 1H), 3.36 (dd, J=14.0 and 4.4 Hz, 1H), 3.11 (dd, J=14.0 and 8.8 Hz, 1H).

Workup

  1. temperaturethen cooled to −45° C
  2. stirringthe reaction mixture stirred for 30 min at this temperature
  3. customthe solvent was removed in vacuo
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-99ef7ecdc9254e2f9c494a0c053ab716
Source dataset
uspto-grants-2010_05
Patent number
US07718682B2

Linked notes

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