Potassium Carbonate → HCID 89690204, compound

HRID 714030Notes

Reaction equation

HRID 714030 reaction equation
[OH:1][C:2]1[C:3]([CH2:12][CH2:13][CH3:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:15]([O:22][C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][CH2:32]Cl)[C:26]([CH2:34][CH3:35])=[CH:25][C:24]=1[C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].COC(C)(C)C>CS(C)=O.CN(C)C1C=CN=CC=1.O>[CH2:15]([O:22][C:23]1[C:24]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)=[CH:25][C:26]([CH2:34][CH3:35])=[C:27]([CH:28]=1)[O:29][CH2:30][CH2:31][CH2:32][O:1][C:2]1[C:3]([CH2:12][CH2:13][CH3:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 10715904HCID 10715904, compoundHCID 85701783HCID 85701783, compound

Product 1

HCID 89690204HCID 89690204, compoundYield 107.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-hydroxy-2-propyl-benzoate (40.0 g, 206 mmol) and 1-benzyloxy-5-(3-chloropropoxy)-4-ethyl-2-(4-fluorophenyl)benzene (prepared according to Org. Process Res. Dev. (2009), 13: 268-275) (82.15 g, 206 mmol) in dimethylsulfoxide (240 mL) add potassium carbonate (30.2 g, 219 mmol) and N,N-dimethylpyridin-4-amine (2.0 g, 16 mmol) in succession. Stir the suspension for 87 h at 60° C. and then allow it to cool. Dilute the mixture with water (600 mL) and with methyl-tert-butylether (100 mL) and stir for 15 min. Separate the phases and wash the aqueous portion with methyl-tert-butylether (3×30 mL). Wash the combined organic extracts with water and brine. Concentrate the organic portion in vacuo to yield the title compound (123.0 g, quantitative) as a brown oil. ES/MS m/z 557 (M+1).

Workup

  1. temperatureto cool
  2. customSeparate the phases
  3. washwash the aqueous portion with methyl-tert-butylether (3×30 mL)
  4. washWash the combined organic extracts with water and brine
  5. concentrationConcentrate the organic portion in vacuo

Sources & evidence

ORD record
ord-3d958daacc1f4d8e871a436958fd40ab
Source dataset
uspto-grants-2015_11
Patent number
US09187411B2

Reaction notes

Loading…