Triethylamine → HCID 86717348, compound

HRID 527153Notes

Reaction equation

HRID 527153 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:11]1([NH:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27])[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].C(N(CC)CC)C.[C:36](Cl)(=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38]>C(Cl)Cl>[O:21]=[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[C:11]1([C:3]1[CH:4]=[CH:5][C:6]([CH:8]([CH3:10])[CH3:9])=[CH:7][C:2]=1[O:1][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[NH:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86717349HCID 86717349, compound

Product 1

HCID 86717348HCID 86717348, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of pentanoic acid [2-(2-hydroxy-4-isopropyl-phenyl)-1,3-dioxo-indan-2-yl]-amide (0.10 g, 0.26 mmol) in anhydrous methylene chloride (10 ml) was added triethylamine (0.03 g, 0.31 mmol) and pivaloyl chloride (0.047 g, 0.39 mmol) and then stirred for 2 hrs. The reaction mixture was concented and extracted with ethylacetate. The concentrated organic layer was purified using silica gel column chromatography (ethylacetate:hexane=1:4) to afford the title compound (0.11 g, 91%).

Workup

  1. extractionextracted with ethylacetate
  2. customThe concentrated organic layer was purified

Sources & evidence

ORD record
ord-2918f33371854eb18d6c190c5bd463cf
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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