Sodium Iodide → HCID 69931180, compound

HRID 1604463Notes

Reaction equation

HRID 1604463 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:17]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][C:13]([O:25][CH3:26])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl.Cl[CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:37][CH2:38][N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][C:13]([O:25][CH3:26])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 131721471HCID 131721471, compound

Product 1

HCID 69931180HCID 69931180, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (±)-cis-3-(4-fluorophenyl)-4-(4-hydroxyphenyl)-7-methoxy-chromane, (0.53 9, 1.51 mmol) potassium carbonate, (2.10 g, 15.2 mmol) sodium iodide, (0.01 g, 0.07 mmol) 1-(2-chloroethyl)pyrrolidine hydrochloride, (0.28 g, 1.65 mmol) and acetone, (35 ml) was stirred at 60° C., under reflux, for 24 h. The resulting mixture was filtered and the solvent evaporated to give a colourless gum, which solidified on cooling. The crude solid was recrystallised from aqueous ethanol to give the product as colourless needles, which were vacuum dried.

Workup

  1. temperatureunder reflux, for 24 h
  2. filtrationThe resulting mixture was filtered
  3. customthe solvent evaporated
  4. customto give a colourless gum, which
  5. temperatureon cooling
  6. customThe crude solid was recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-df46c6de5c6d40249058b96138b26217
Source dataset
uspto-grants-1999_11
Patent number
US05994390

Reaction notes

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