Methyl chloroformate → HCID 71478040, compound

HRID 527164Notes

Reaction equation

HRID 527164 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](Cl)=[O:11].[OH:13][C:14]12[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[C:18]1([NH:27][C:28](=[O:30])[CH3:29])[C:17]1[CH:31]=[CH:32][C:33]([CH:35]([CH3:37])[CH3:36])=[CH:34][C:16]=1[O:15]2>C1COCC1>[C:10](=[O:11])([O:9][CH3:8])[O:15][C:16]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:32]=[CH:31][C:17]=1[C:18]1([NH:27][C:28](=[O:30])[CH3:29])[C:19](=[O:26])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]1=[O:13]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86716885HCID 86716885, compound

Product 1

HCID 71478040HCID 71478040, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.24 ml, 1.77 mmol) and methylchloroformate (0.11 ml, 1.48 mmol) were added to N-(4b-hydroxy-7-isopropyl-10-oxo-9b,10-dihydro-4bH-benzo[d]indeno[1,2-b]furan-9b-yl)acetamide (0.50 g, 1.48 mmol) in THF (5 ml). The reaction mixture was stirred at room temperature for 12 hrs, concentrated in a vacuum to remove solvent. The reaction mixture was extracted with water and methylene chloride, and purified through silica gel column chromatography (ethylacetate:hexane=1:2) to afford the title compound (0.10 g, 14%).

Workup

  1. concentrationconcentrated in a vacuum
  2. customto remove solvent
  3. extractionThe reaction mixture was extracted with water and methylene chloride
  4. custompurified through silica gel column chromatography (ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-38e513f8545144179ff447d6f320e3d8
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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