Potassium Carbonate → HCID 56599937, compound

HRID 514080Notes

Reaction equation

HRID 514080 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[CH3:31]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+].CC#N.O>C1(C)C=CC=CC=1.C(O)C.O>[C:26]([O:25][CH:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([CH3:31])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:20]([OH:22])=[O:21])([CH3:27])([CH3:29])[CH3:28]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 18373917Acetonitrile--water (1/1)HCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 56599937HCID 56599937, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-tert-Butoxy-2-(1-(4-chlorophenyl)-3,7-dimethylnaphthalen-2-yl)acetic acid (78) was prepared by the method of Example 67 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate using trimethylboroxine and K2CO3 instead of triethylamine, and toluene, ethanol, water as a solvent mixture. 1H-NMR: 400 MHz, (CD3OD) δ: 7.65 (d, J=8 Hz, 1H), 7.61 (s, 1H), 7.53 (m, 3H), 7.27 (m, 2H), 6.98 (s, 1H), 5.15 (s, 1H), 2.56 (s, 3H), 2.30 (s, 3H), 0.96 (s, 9H). HPLC (Kinetex 2.6u, 50×4.6 mm, 2-100% MeCN/H2O+0.05% HOAc, 5 min run): tR (min)=4.06.

Sources & evidence

ORD record
ord-4f946e92c995496a9a2d3385a8d1f023
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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