1,3-Propanedithiol → Ethyl (E)-4-[-2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-(1,3-dithian-2-yl)naphthalen-2-yl)ethenyl]benzoate

HRID 1953870노트

반응식

HRID 1953870 반응식
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9](=O)[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.[CH3:27]C1(C)CCC(=O)C2C=C(/C=C/C3C=CC(C(O)=O)=CC=3)C=CC1=2.[CH2:51]([SH:55])[CH2:52][CH2:53][SH:54]>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][CH:9]([CH:27]2[S:55][CH2:51][CH2:52][CH2:53][S:54]2)[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

6

반응물 3

HCID 80131,3-PropanedithiolHCID 12069038Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoateHCID 12069039(E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoic acid

생성물 1

HCID 19695066Ethyl (E)-4-[-2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-(1,3-dithian-2-yl)naphthalen-2-yl)ethenyl]benzoate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 11430Potassium Carbonate용매

실험 절차

To a cold solution (0 ° C.) of 140 mg (0.40 mmol) of ethyl (E)4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2), in 6.0 mL of methylene chloride was added dropwise 130 mg (0.12 mL, 1.2 mmol) of 1,3-propanedithiol and 0.17g (0.15 mL, 102 mmol) of borontrifluoride diethyl etherate. The reaction stirred between 0 ° C. and room temperature for 4 h. The mixture was diluted with aqueous sat. potassium carbonate, and extracted with ether (2x). The organic phase was washed with brine, dried over MgSO4 and then concentrated in vacuo. The crude product was purified by flash chromatography (silica, 10 % ethyl acetate in hexane) to afford the title compound as a solid.

후처리

  1. extractionextracted with ether (2x)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (silica, 10 % ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-097786b3e7694a0ab40c4631aa6404c4
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06117987

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