Potassium Carbonate → HCID 19046267, compound

HRID 1781320Notes

Reaction equation

HRID 1781320 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Br)[CH3:2].[O:10]1[C:19]2[C:14](=[C:15]([NH2:20])[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:10]1[C:19]2[C:14](=[C:15]([NH:20][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 18739714HCID 18739714, compound

Product 1

HCID 19046267HCID 19046267, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Bromoacetaldehyde diethyl acetal (11.8 ml) was added to a mixture of chroman-5-yl-amine (5.85 g) (prepared according to J. Heterocyclic Chem., (1973), Vol 10 (4) page 623), and potassium carbonate (10.84 g) in dry DMF (70 ml) at room temperature under N2. The mixture was heated at 100° C. for 60 h. The cooled mixture was partitioned between water (800 ml) and ether (3×200 ml). The combined organic extracts were washed with brine/water 1:1 (2×200 ml) and dried. The solvent was evaporated and the residue purified by flash column chromatography on silica. Elution with cyclohexane/ethyl acetate 6:1 gave the title compound as a pale yellow oil (8.0 g).

Workup

  1. customThe cooled mixture was partitioned between water (800 ml) and ether (3×200 ml)
  2. washThe combined organic extracts were washed with brine/water 1:1 (2×200 ml)
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue purified by flash column chromatography on silica
  6. washElution with cyclohexane/ethyl acetate 6:1

Sources & evidence

ORD record
ord-327e2608ec0144c2b599ca59201375d2
Source dataset
uspto-grants-1997_05
Patent number
US05633276

Reaction notes

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