Methyl iodide → methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

HRID 22190

반응식

HRID 22190 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH3:12][O:13][C:14](=O)[O:15]C.[H-].[Na+].[CH3:20]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([CH3:20])([C:14]([O:13][CH3:12])=[O:15])[CH2:5]2

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanone

생성물 1

HCID 19384693methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 8.0 g of 5-chloroindanone and 4.2 ml of dimethylcarbonate in 60 ml of THF was added 4.0 g of 60% NaH and the mixture was heated to reflux under N2 overnight. After this time the reaction was cooled to room temperature and 4.0 ml of methyl iodide was added and the mixture was reheated to reflux overnight. The reaction was then cooled and partitioned between ether and 5% aqueous NaHCO3 and the aqueous extracts were washed twice with ether. The combined aqueous extracts were dried over MgSO4 and concentrated to 11.24 g of a brown oil. Chromatogrpahy on silica gel (10% ethyl acetate/hexane) afforded 4.25 g of the title compound as a brown oil. 1H NMR (CDCl3) δ 1.52 (s, 3H), 2.96 (d, 1H), 3.68 (s, 3H), 3.69 (d, 1H), 7.40 (d, 1H), 7.47 (s, 1H), 7.71 (d, 1H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux under N2 overnight
  3. temperatureto reflux overnight
  4. temperatureThe reaction was then cooled
  5. custompartitioned between ether and 5% aqueous NaHCO3
  6. washthe aqueous extracts were washed twice with ether
  7. dry with materialThe combined aqueous extracts were dried over MgSO4
  8. concentrationconcentrated to 11.24 g of a brown oil

출처 및 근거

ORD 기록
ord-419a3f8533f6491a8575202ffbe54415
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428027

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