Phosphorus pentachloride → Spiro[cyclobutane-1,2'-thiochroman]-4'-one

HRID 1175763Notes

Reaction equation

HRID 1175763 reaction equation
[C:1]1([S:7][C:8]2([CH2:12][C:13]([OH:15])=O)[CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[O:15]=[C:13]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=2[S:7][C:8]2([CH2:9][CH2:10][CH2:11]2)[CH2:12]1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 667456062-[1-(Phenylsulfanyl)cyclobutyl]acetic acid

Product 1

HCID 66746475Spiro[cyclobutane-1,2'-thiochroman]-4'-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-Phenylthiocyclobutane-1-acetic acid (10 mmol) in benzene was treated with excess of PCl5 at room temperature for 15 h. The reaction mixture was concentrated under vacuum and the residue was again dissolved in benzene. AlCl3 was then added to the solution and it was stirred for 24 h at room temperature. The reaction mixture was diluted with excess of ethyl acetate and washed with water and brine. Organic layer was then separated, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to afford the desired compound as oil.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue was again dissolved in benzene
  3. additionAlCl3 was then added to the solution and it
  4. additionThe reaction mixture was diluted with excess of ethyl acetate
  5. washwashed with water and brine
  6. customOrganic layer was then separated
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5a8fcbcbf11c4db6b57480048f50bff0
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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