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 1953870ノート

反応式

HRID 1953870 の反応式
[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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 11430Potassium Carbonate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-097786b3e7694a0ab40c4631aa6404c4
出典データセット
uspto-grants-2000_09
特許番号
US06117987

反応ノート

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