Hydrochloric Acid → HCID 22490824, compound

HRID 2180596Notes

Reaction equation

HRID 2180596 reaction equation
[H-].[Na+].C(S)C.[Br:6][C:7]1[C:16]2[C:15]([CH3:18])([CH3:17])[CH2:14][CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=2[CH:10]=[C:9]([C:22](=[O:24])[CH3:23])[C:8]=1[O:25]C.Cl>CCCCCC.CN(C)C=O>[Br:6][C:7]1[C:16]2[C:15]([CH3:18])([CH3:17])[CH2:14][CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:11]=2[CH:10]=[C:9]([C:22](=[O:24])[CH3:23])[C:8]=1[OH:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 22490934HCID 22490934, compound

Product 1

HCID 22490824HCID 22490824, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (1.07 g, 26.64 mmol) was rinsed with hexane and suspended in dry N,N-dimethylformamide (80 mL). To the suspension was added ethanethiol (1.9 mL, 26.6 mmol) and stirred at room temperature for 30 min, which resulted in the formation of a clear solution. A solution of 1-(4-bromo-8-isopropyl-3-methoxy-5,5-dimethyl-5,6-dihydronaphthalen-2-yl)-ethanone (Compound A-103,2.6 g, 7.4 mmol) in N,N-dimethylformamide (10 mL) was added to the solution and the mixture was heated at 130° C. for 5 h. The mixture was cooled to room temperature, acidified with 10% HCl and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 5% ethyl acetate in hexane) to yield the title compound as a brown oil.

Workup

  1. customwhich resulted in the formation of a clear solution
  2. temperaturethe mixture was heated at 130° C. for 5 h
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with diethyl ether
  5. washThe combined ethereal layers were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography (silica gel, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c1aa852fca4f47ad8119330bedcc3dca
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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