Tetrahydrofuran → HCID 21528437, compound

HRID 1658641Notes

Reaction equation

HRID 1658641 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[Cl-].[NH4+].[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:23]1[O:19][CH2:20][C:21]#[C:22][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 110751355-Chloro-5H-dibenzo[a,d][7]annulene

Product 1

HCID 21528437HCID 21528437, compound

Procedure

This preparation illustrates methods according to step 1 of the process for preparing the compounds of formula A. In this preparation a solution containing 8 g. of 5-chloro-5H-dibenzo[a,d]cycloheptene in 200 ml. of anhydrous tetrahydrofuran is added dropwise, under nitrogen, to a stirred solution containing 0.042 moles of 3-(2-tetrahydropyranyloxy)-prop-1-ynyl-1-magnesium chloride in 210 ml. of anhydrous tetrahydrofuran, at room temperature. The resulting mixture is heated for 2 hours at reflux and then allowed to stand, with stirring, for 16 hours at room temperature. The reaction mixture is then treated, first with 25 ml. of saturated aqueous ammonium chloride solution, then with 75 ml. of water, and then concentrated under reduced pressure to remove most of the organic solvent resulting in a two-phase liquid-liquid system, which is then shaken and extracted with three 60 ml. portions of ethyl ether. The ethereal extracts are combined and washed consecutively with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine. The washed extracts are dried over sodium sulfate-potassium carbonate and then evaporated under reduced pressure affording a residue of 5-[3-(2-tetrahydropyranyloxy)-prop-1-ynyl]-5H-dibenzo[a,d] cycloheptene, which is divided into two portions, one of which is further purified by column chromatography on silica gel. The other portion is used directly as starting material for the next step.

Workup

  1. customaccording to step 1 of the process for preparing the compounds of formula A
  2. customIn this preparation a solution
  3. additioncontaining 8 g
  4. customat room temperature
  5. temperatureThe resulting mixture is heated for 2 hours
  6. temperatureat reflux
  7. additionThe reaction mixture is then treated, first with 25 ml
  8. concentrationof water, and then concentrated under reduced pressure
  9. customto remove most of the organic solvent
  10. customresulting in a two-phase liquid-liquid system, which
  11. stirringis then shaken
  12. extractionextracted with three 60 ml
  13. washwashed consecutively with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine
  14. dry with materialThe washed extracts are dried over sodium sulfate-potassium carbonate
  15. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e24d88d9446a44af92c25f46c0a8d34d
Source dataset
uspto-grants-1976_06
Patent number
US03965181

Reaction notes

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