HCID 21477178, compound → HCID 54730488, compound

HRID 2293683Notes

Reaction equation

HRID 2293683 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.Br[CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1)[CH2:15][CH3:16].CC(C1C(=O)OC2C(C=1O)=CC=CC=2)(C)C1C=CC=CC=1>C(Cl)Cl>[Br:23][C:19]1[CH:18]=[C:17]([CH:14]([C:3]2[C:4](=[O:12])[O:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:15][CH3:16])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 21477178HCID 21477178, compoundHCID 546829304-HydroxycoumarinHCID 54724919HCID 54724919, compound

Product 1

HCID 54730488HCID 54730488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 4-hydroxycoumarin (898 mg) and 1-bromo-1-(3-bromophenyl)propane of Preparation 39 (3.08 g) under nitrogen is sealed in a screw-cap vial and placed in an oil bath at 100° C. The mixture is heated to 175° C. over approximately 45 rain, and the resulting melt is stirred at this temperature for 45 rain, cooled to RT, diluted with methylene chloride (45 mL), washed with water (10 mL) and saline (10 mL), dried over sodium sulfate, and concentrated under reduced pressure to give a residue which is then chromatographed on silica gel (230-400 mesh, 350 g), eluting with a gradient of ethyl acetate/hexane (15/85-60/40). Pooling of fractions with an Rf =0.20 by TLC (ethyl acetate/hexane, 50/50) and removal of solvent gives the title compound.

Workup

  1. customis sealed in a screw-cap vial and
  2. customplaced in an oil bath at 100° C
  3. temperaturecooled to RT
  4. washwashed with water (10 mL) and saline (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue which
  8. customis then chromatographed on silica gel (230-400 mesh, 350 g)
  9. washeluting with a gradient of ethyl acetate/hexane (15/85-60/40)
  10. customPooling of fractions with an Rf =0.20 by TLC (ethyl acetate/hexane, 50/50) and removal of solvent

Sources & evidence

ORD record
ord-78796e94b9ac429db10b7d59d328d0e6
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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