tert-Butoxy bis(dimethylamino)methane → HCID 87429210, compound

HRID 2173155Notes

Reaction equation

HRID 2173155 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[O:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[C:17]([O:21]C(N(C)C)N(C)C)(C)(C)C>CN(C=O)C.Cl>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([CH2:1][CH:17]=[O:21])=[CH:3][C:4]=2[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7]1

Participants

5

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 11789046HCID 11789046, compound

Product 1

HCID 87429210HCID 87429210, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 9-methyl-6H-benzo[c]chromen-6-one (100 mg, 0.476 mmol) in dry DMF (2378 μl) Was treated with TERT-BUTOXY BIS(DIMETHYLAMINO)METHANE (99 mg, 0.571 mmol) at 80° C. in a sealed tube for one hour. The solution turned a deep red color and was cooled, diluted with 2M HCl and stirred for 20 minutes. The solution was then extracted with DCM, the combind orgainc layers were dried, filtered and concentrated with out heat. Crude (6-oxo-6H-benzo[c]chromen-9-yl)acetaldehyde was used without further purification. LC-MS (IE, m/z): 239 [M+1]+.

Workup

  1. temperaturewas cooled
  2. extractionThe solution was then extracted with DCM
  3. customthe combind orgainc layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated with
  6. temperatureout heat
  7. customCrude (6-oxo-6H-benzo[c]chromen-9-yl)acetaldehyde was used without further purification

Sources & evidence

ORD record
ord-cfd0876c7cdf424a90f19b890966e43a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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