Potassium Carbonate → HCID 59166712, compound

HRID 1442688Notes

Reaction equation

HRID 1442688 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:24][CH3:25])([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=3)[CH2:14][CH3:15])=[N:10][C:9]=2[CH:26]=1)=[O:4].Br[CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[K+].[K+]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:18]([CH3:23])[CH:17]=3)([CH2:24][CH3:25])[CH2:14][CH3:15])=[N:10][C:9]=2[CH:26]=1)=[O:4]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 59166716HCID 59166716, compound

Product 1

HCID 59166712HCID 59166712, compoundYield 95.1%

Procedure

2-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-benzooxazole-5-carboxylic acid methyl ester (2.10 g, 5.94 mmol) and 1-bromopinacolone (1.59 g, 8.87 mmol) and K2CO3 (2.04 g, 14.8 mmol) are reacted analogous to Example 1, step G to give the title compound as a pale yellow oil (2.55 g, 95%). H-NMR (ppm, CDCl3) δ: 8.43 (1H, d, J=1.3 Hz), 8.01 (1H, dd, J=1.8, 8.8 Hz), 7.42 (1H, d, J=8.4 Hz), 7.01 (1H, d, J=2.2 Hz), 6.96 (1H, dd, J=2.2, 8.4 Hz), 6.51 (1H, d, J=8.8 Hz), 4.84 (2H, s), 3.95 (3H, s), 2.38 (2H, q, J=7.5 Hz), 2.32 (2H, q, J=7.5 Hz), 2.25 (3H, s), 1.25 (9H, s), 0.76 (6H, t, J=7.5 Hz).

Sources & evidence

ORD record
ord-bcc339ffa5c04bf7a29040b84f85cce4
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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