P-Cresol → Ethyl 3-(4-benzyloxyphenyl)-2-(4-methylphenoxy)propionate

HRID 1860059Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:28]S(C)(=O)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:33]1[C:38](O)=[CH:37][CH:36]=[C:35]([CH3:40])[CH:34]=1>CN(C)C=O>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:28][C:38]2[CH:37]=[CH:36][C:35]([CH3:40])=[CH:34][CH:33]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium carbonate (8.09 g) was added to a solution of ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate (11.1 g), which is the product of Reference example 35(a), and p-cresol (2.85 g) in N,N-dimethylformamide (110 ml). This mixture was stirred at 70° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel column using hexane/ethyl acetate=9/1 as the eluant to afford the desired compound (2.84 g) as a colorless oil.

Workup

customThe reaction mixture was partitioned between ethyl acetate and water
customthe layers were separated
dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified via chromatography on silica gel column

Sources & evidence

ORD record: ord-272c04313cbb47389ede0eb8bedb13a2
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Reaction notes

Loading…