Potassium tert-butoxide → HCID 178441596, compound

HRID 928121Notes

Reaction equation

HRID 928121 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[Br:7][C:8]1[S:12][C:11]([C:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)=O)=[N:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.[Cl-].[NH4+]>[Br:7][C:8]1[S:12][C:11]([CH:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:3][CH:2]=[CH2:1])=[N:10][CH:9]=1

Participants

6

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178472369HCID 178472369, compound

Product 1

HCID 178441596HCID 178441596, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 1140TolueneSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-10 °C

Procedure

Methyltriphenylphosphonium bromide (2.58 g, 7.22 mmol), potassium tert-butoxide (0.8248 g, 7.35 mmol) and toluene (24 ml) were combined and heated under reflux for 1 h. Then, the mixture was cooled to −10° C. and ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl) carbonyl]cyclohexane-carboxylate (1.022 g, 2.95 mmol) in 2 ml of toluene was added dropwise. The mixture was stirred between 2° C. to 3° C. for 1.5 h. The reaction was diluted with aqueous saturated ammonium chloride, extracted with EtOAc (2×) and the combined organic phases were washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified on silica gel (0-8% EtOAc in hexane) to afford ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)but-3-en-1-yl]cyclohexanecarboxylate. MS ESI calc'd. for C16H22BrNO2S [M+H]+ 372, 374. found 372, 374. 1H NMR (500 MHz, CDCl3) δ 7.56 (s, 1H), 5.65 (dd, J=6.9, 10.2, 1H), 5.13-4.79 (m, 2H), 4.10 (q, J=7.1, 2H), 2.97-2.89 (m, 1H), 2.62-2.38 (m, 2H), 2.23-1.86 (m, 4H), 1.70-1.60 (m, 2H), 1.50-1.28 (m, 2H), 1.23 (t, J=7.0, 3H), 1.12-0.92 (m, 2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. extractionextracted with EtOAc (2×)
  4. washthe combined organic phases were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel (0-8% EtOAc in hexane)

Sources & evidence

ORD record
ord-2821f1abd377408aaa5ae512fd0353e8
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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