HCID 178488804, 화합물 → HCID 178488805, 화합물

HRID 1489200노트

반응식

HRID 1489200 반응식
[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]

참가 물질

4

반응물 1

HCID 178488804HCID 178488804, 화합물

생성물 1

HCID 178488805HCID 178488805, 화합물수율 75.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a2b7e3952f094e9ea84692432992d3f6
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05677336

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