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

HRID 1175763
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HRID 1175763 반응식
[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
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a8fcbcbf11c4db6b57480048f50bff0
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842703B2

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