Triethylamine → HCID 71477289, compound

HRID 527148Notes

Reaction equation

HRID 527148 reaction equation
[NH2:1][C:2]12[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:3]1([OH:22])[O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=12.C(N([CH2:28][CH3:29])CC)C.[C:30](Cl)(=[O:35])[CH2:31][CH2:32][CH2:33][CH3:34]>ClCCl>[C:30]([O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[C:2]1([NH:1][C:3](=[O:4])[CH2:2][CH2:6][CH2:28][CH3:29])[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:3]1=[O:22])(=[O:35])[CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 86716884HCID 86716884, compound

Product 1

HCID 71477289HCID 71477289, compoundYield 129.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9b-amino-4b-hydroxy-7-isopropyl-4bH-benzo[d]indeno[1,2-b]furan-10(9bH)-one (0.15 g, 0.50 mmol) in dichloromethane (5 ml) was added triethylamine (0.21 mL, 1.52 mmol) and valeroyl chloride (74 μL, 0.61 mmol) at 0° C. and then stirred for overnight at room temperature. The reaction mixture was extracted with dichloromethane and purified using silica gel column chromatography (30% ethylacetate in hexane) to afford the title compound (150 mg, 68%).

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane
  2. custompurified

Sources & evidence

ORD record
ord-0ac20147d46b46b98b14242b98a9c8d1
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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