Diethyl Ether → 1-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

HRID 1684028ノート

反応式

HRID 1684028 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]2[CH2:30][S:29]C(=S)[S:27]2)[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][O:22][CH3:23]>C1COCC1>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:26]([SH:27])[CH2:30][SH:29])[CH:17]=[C:18]([O:24][CH3:25])[C:19]=1[O:20][CH2:21][O:22][CH3:23]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 190418014-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,3-dithiolane-2-thioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 190418081-(3,5-Dimethoxy-4-methoxymethoxyphenyl)-1,2-ethanedithiol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Lithium aluminum hydride (0.622 g, 16.38 mmole) is added to 60 ml dry diethyl ether. To this slurry is added dropwise 4-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1,3-dithiolane-2-thione (33) (3.40 g, 10.24 mmole) predissolved in 35 ml dry THF. The reaction is stirred under an N2 atmosphere until the solution becomes colorless (4 hours). The reaction is cooled to 0° C. and the excess hydride destroyed with H2O. The reaction mixture is acidified with 10% HCl and immediately extracted with diethyl ether. The organic layer is washed with H2O, dried over MgSO4, filtered and evaporated to a white solid (2.47 g, 84%). NMR: (CDCl3) 2.33,d,1H;2.90,m,1H;3.10,m,1H; 3.59,s,3H;3.85,s,6H;4.03,m,1H;5.10,s,2H;6.53,s,2H Melting Point: 84°-85° C. C,H,S analysis: (theoretical, actual) C (49.63,49.52); H (6.25,6.28); S (22.08,22.16).

後処理

  1. custom(4 hours)
  2. customthe excess hydride destroyed with H2O
  3. extractionimmediately extracted with diethyl ether
  4. washThe organic layer is washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to a white solid (2.47 g, 84%)

出典と根拠

ORDレコード
ord-e1fda570ebe5467995354f390c3047b0
出典データセット
uspto-grants-1997_06
特許番号
US05639782

反応ノート

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