Hydrochloric Acid → Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

HRID 900761

반응식

HRID 900761 반응식
[S:1]1[CH2:6][CH2:5][CH:4]([C:7]#N)[CH2:3][CH2:2]1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC[O:19]CC.Cl>C1COCC1.[Cu]I>[C:9]1([C:7]([CH:4]2[CH2:5][CH2:6][S:1][CH2:2][CH2:3]2)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21598641Thiane-4-carbonitrileHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 69290818Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Tetrahydro-2H-thiopyran-4-carbonitrile (2.6 g, 20.5 mmol) and CuI (195 mg, 1 mmol) were diluted in dry THF (200 ml). A 1M solution of phenyl magnesium bromide in THF (41 ml, 41 mmol) was added and the mixture was heated at reflux for 16 hours. After cooling at room temperature, ether was added and the imine was hydrolyzed with a 1 N HCl solution for 10 minutes. The organic phase was separated and treated with a 0.1 N HCl solution for 10 minutes. The organic phase was separated and washed with brine, dried over MgSO4 and evaporated in vacuum. After chromatography on silica gel (CH2Cl2/hexane 30/70), the phenyl(tetrahydro-2H-thiopyran-4-yl)methanone 17 was obtained as a white solid (3 g, 70%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe organic phase was separated
  4. additiontreated with a 0.1 N HCl solution for 10 minutes
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuum

출처 및 근거

ORD 기록
ord-dfd66986ba0d4db5a9580e8fab9bfee8
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361668B2

연결된 노트

불러오는 중…