Triethylamine → HCID 90097583, compound

HRID 527149Notes

Reaction equation

HRID 527149 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[C:10]2=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:6]=1.C(N([CH2:28][CH3:29])CC)C.[C:30](Cl)(=[O:34])[CH2:31][CH2:32][CH3:33].[CH2:36]([O:38]C(=O)C)[CH3:37]>C(Cl)Cl>[C:30]([NH:1][C:2]1([C:10]2[CH:9]=[CH:8][C:7]([CH:11]([CH3:12])[CH3:13])=[CH:6][C:5]=2[O:4][C:36](=[O:38])[CH2:37][CH2:28][CH3:29])[C:3](=[O:22])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]1=[O:21])(=[O:34])[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 86716884HCID 86716884, compound

Product 1

HCID 90097583HCID 90097583, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9b-amino-4b-hydroxy-7-isopropyl-4b,9b-dihydro-5-oxa-indeno[2,1-a]inden-10-one (0.20 g, 0.67 mmol) in anhydrous methylene chloride (10 ml) was added triethylamine (0.20 g, 2.01 mmol) and butyryl chloride (0.18 g, 1.69 mmol) at room temperature and then stirred for 3 hrs. The reaction mixture was diluted in ethylacetate, and washed with water several time. The organic layer was dried, filtered, and purified using silica gel column chromatography (ethylacetate:hexane=1:4 to 1:2) to afford the title compound (230 mg, 79%).

Workup

  1. washwashed with water several time
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. custompurified

Sources & evidence

ORD record
ord-59e2b49a4e0446d4ad1442e0e4942846
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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