Triethylamine → HCID 58509686, compound

HRID 72305Notes

Reaction equation

HRID 72305 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:8][C:9]1[C:14]([CH:15]2[C:21](=[O:22])[CH:20]3[CH2:23][CH:17]([CH2:18][CH2:19]3)[C:16]2=[O:24])=[C:13]([CH3:25])[CH:12]=[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:10]=1.C(N(CC)CC)C>ClCCl>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:24][C:16]1[CH:17]2[CH2:23][CH:20]([C:21](=[O:22])[C:15]=1[C:14]1[C:9]([CH3:8])=[CH:10][C:11]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:12][C:13]=1[CH3:25])[CH2:19][CH2:18]2)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 913541313-(3,5-Dimethylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 58509686HCID 58509686, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pivaloyl chloride (248 μl, 2 mmol) is added to a solution of 3-(3,5-dimethylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione (148 mg, 0.46 mmol) in dichloromethane (10 ml) and triethylamine (280 μl, 2 mmol) at room temperature. The reaction mixture is stirred at room temperature overnight. The reaction mixture is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel to afford 3-(3,5-dimethylbiphen-4-yl)-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl 2,2-dimethylpropionate.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-add2a2de59424cbea63eef7244463b4f
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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