Dichloromethane → HCID 15491039, compound

HRID 1782540Notes

Reaction equation

HRID 1782540 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][C:11]([OH:13])=[O:12].[C:14](Cl)(=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.[Sn](Cl)(Cl)(Cl)Cl.[CH2:30](Cl)Cl>>[CH3:30][O:12][C:11](=[O:13])[CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]=1[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 111058882-(1-Benzofuran-2-yl)acetic acid

Product 1

HCID 15491039HCID 15491039, compound

Conditions

Temperature
2.5 °C

Procedure

To the BFAA methyl ester from Step 1 (assumed 1× mole fraction) was added p-anisoyl chloride (approximately 1.08 parts by weight; 1.1× mole fraction), followed by methylene chloride (approximately 3.11 parts by weight). The mixture was stirred and cooled to about 0-5° C. Tin(IV) chloride (approximately 1.46 parts by weight) was added while controlling the batch temperature below about 10° C. The reaction was stirred at about 0-10° C. for about 3 hours then was warmed and stirred at about 20-25° C. for several hours. Methylene chloride was added and the reaction was cooled and quenched with 4% aqueous hydrochloric acid while controlling the temperature to below about 10° C. The organic layer was separated and washed with water. The organic layer was concentrated under vacuum and dried by distillation of more methylene chloride. The resulting product was dissolved in methylene chloride and transferred to a clean vessel.

Workup

  1. customthe batch temperature below about 10° C
  2. stirringThe reaction was stirred at about 0-10° C. for about 3 hours
  3. temperaturethen was warmed
  4. stirringstirred at about 20-25° C. for several hours
  5. temperaturethe reaction was cooled
  6. customquenched with 4% aqueous hydrochloric acid
  7. customto below about 10° C
  8. customThe organic layer was separated
  9. washwashed with water
  10. concentrationThe organic layer was concentrated under vacuum
  11. dry with materialdried by distillation of more methylene chloride
  12. dissolutionThe resulting product was dissolved in methylene chloride
  13. customtransferred to a clean vessel

Sources & evidence

ORD record
ord-fd8775bd22e142a9814d78f79ee99f8a
Source dataset
uspto-grants-2009_03
Patent number
US07498449B2

Reaction notes

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