Potassium Carbonate → HCID 59166708, compound

HRID 1442683Notes

Reaction equation

HRID 1442683 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]=[C:10]([C:12]([CH2:23][CH3:24])([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH3:22])[CH:16]=3)[CH2:13][CH3:14])[O:11][C:7]=2[CH:6]=1)=[O:4].Br[CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[N:9]=[C:10]([C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:17]([CH3:22])[CH:16]=3)([CH2:13][CH3:14])[CH2:23][CH3:24])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 59166713HCID 59166713, compound

Product 1

HCID 59166708HCID 59166708, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-benzooxazole-6-carboxylic acid methyl ester (1.20 g, 3.38 mmol) in acetone (40 mL) is treated with 1-bromopinacolone (0.73 g, 4.06 mmol) and K2CO3 (0.93 g, 6.76 mmol). The suspension is stirred at RT for 4 h. The mixture is filtered, and the filtrate is concentrated. The residue is purified using silica gel column chromatography (15% EtOAc/Hex) to give the title compound as a pale yellow oil (1.50 g, 98%). H-NMR (ppm, CDCl3) δ: 8.14 (1H, d, J=2.4 Hz), 8.07 (1H, dd, J=1.2, 8.4 Hz), 7.78 (1H, d, J=8.4 Hz), 7.05 (1H, d, J=1.6 Hz), 7.00 (1H, dd, J=2.4, 8.4 Hz), 6.56 (1H, d, J=8.4 Hz), 4.87 (2H, s), 3.96 (3H, s), 2.40 (2H, q, J=7.5 Hz), 2.30 (2. H, q, J=7.5 Hz), 2.28 (3H, s), 1.27 (9H, s), 0.77 (6H, t, J=7.5 Hz).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified

Sources & evidence

ORD record
ord-9e2c5bc5d04b48779a9aaf2fba71e858
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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