Dimethylformamide → HCID 15729794, compound

HRID 1904552Notes

Reaction equation

HRID 1904552 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([OH:12])=[CH:11][C:4]=2[O:3]1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[OH-].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[CH2:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([O:12][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[CH:11][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 110412812,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-ol

Product 1

HCID 15729794HCID 15729794, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

2,3-Dihydro-2,2-dimethyl-7-hydroxy-4H-1-benzopyran (2.0 g) synthesized as in Referential Example 19, 1.8 g of p-chloronitrobenzene, 0.9 g of potassium hydroxide, 20 ml of N,N-dimethylformamide and 10 ml of toluene were put into a flask equipped with the DeanStark condenser, and were heated to 110° C. While removing evaporated water as an azeotrope with toluene, the reaction was carried out for 1 hour. After cooling, the reaction mixture was poured into water, and extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvents were evaporated. The residue was purified by column chromatography to give 2.8 g (yield 84%) of the desired product as a brown liquid.

Workup

  1. customwere put into a flask
  2. customequipped with the DeanStark condenser
  3. customWhile removing
  4. customevaporated water as an azeotrope with toluene
  5. temperatureAfter cooling
  6. additionthe reaction mixture was poured into water
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract was dried over magnesium sulfate
  9. customthe solvents were evaporated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c47418338bc1479493fceefb2d20359c
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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