HCID 178488804、化合物 → HCID 178488805、化合物

HRID 1489200ノート

反応式

HRID 1489200 の反応式
[C:1]([C:5]1[C:10]([O:11][SiH:12]([CH3:14])[CH3:13])=[C:9]([Br:15])[C:8]([O:16][CH3:17])=[CH:7][C:6]=1[CH2:18][CH:19]1[C:24](=[O:25])[CH:23]=[CH:22][CH2:21][C:20]1([CH3:27])[CH3:26])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([C:5]1[C:10]([O:11][SiH:12]([CH3:13])[CH3:14])=[C:9]([Br:15])[C:8]([O:16][CH3:17])=[CH:7][C:6]=1[CH2:18][CH:19]1[C:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][CH2:23][C:24]1=[O:25])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 1

HCID 178488804HCID 178488804、化合物

生成物 1

HCID 178488805HCID 178488805、化合物収率 75.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a flame-dried round-bottomed flask containing 6-[2'-(tert-butyl)dimethylsilyloxy-4'-bromo-5'-methoxyphenyl]methyl-5,5-dimethylcyclohex-2-en-1-one (13) (0.154 g, 0.454 mmol) in 22 mL ethyl acetate (which had been pre-dried over K2CO3) at room temperature was added 20 mg 5% palladium on carbon, and after flushing / evacuating the vessel 3 times with nitrogen, a hydrogen atmosphere was introduced and maintained by use of a balloon. After 24 h, the flask was again flushed several times with nitrogen, and the contents of the flask were filtered, rinsing with an additional 100 mL ethyl acetate. Rotary evaporation of the solvent afforded 0.156 g (quantitative) of the saturated benzylic ketone as a colorless, viscous oil (Rf 0.67, 2:1 hexanes/ethyl acetate). 1H NMR (400 MHz, CDCl3) δ0.22 and 0.25 [2s, 2×3H, Si(CH3)2 ], 0.87 and 1.12 (2s, 2×3H, geminal-CH3 's), 1.01 [s, 9H, SiC(CH3)3 ], 3.71 (s, 3H, OCH3), 6.79 (s, 1H, 6'-H), 6.91 ppm (s, 1H, 3'-H).

後処理

  1. customafter flushing / evacuating the vessel 3 times with nitrogen
  2. additiona hydrogen atmosphere was introduced
  3. temperaturemaintained by use of a balloon
  4. filtrationthe contents of the flask were filtered
  5. washrinsing with an additional 100 mL ethyl acetate
  6. customRotary evaporation of the solvent

出典と根拠

ORDレコード
ord-a2b7e3952f094e9ea84692432992d3f6
出典データセット
uspto-grants-1997_10
特許番号
US05677336

反応ノート

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