Chloride → 2-tert-Butyl-2,3-dihydro-1H-inden-1-one

HRID 1937031노트

반응식

HRID 1937031 반응식
[Cl-].[CH3:2][Mg]I.[C:5](=[C:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:17])([CH3:7])[CH3:6].[Cl-].[NH4+]>O1CCCC1>[C:5]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:17])([CH3:2])([CH3:7])[CH3:6]

참가 물질

6

반응물 4

HCID 312ChlorideHCID 25517Ammonium ChlorideHCID 15133342-isopropylidene-1-indanoneHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 129273752-tert-Butyl-2,3-dihydro-1H-inden-1-one수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the cupurous chloride (0.258 g, 2.61 mmol) inside 250 mL round bottom flask was added 22 mL of methylmagnesium iodide (3.0 M solution in diethyl ether, 66 mmol) at 0° C. under nitrogen. Diethyl ether was removed in vacuo. Tetrahydrofuran (65 mL) was then introduced. To this resulting suspension was added a solution of 2-isopropylidene-1-indanone (5.00 g, 29 mmol) in Tetrahydrofuran (25 mL) through a dropping funnel dropwise at 0° C. The mixture was stirred at the same temperature for another 1 h and then at ambient temperature overnight (16 h). The slurry was poured into ice (32 g) containing ammonium chloride (6.44 g). The solution was extracted with diethyl ether (5*80 mL). All ethereal layers were combined, washed with water (20 mL), dried over anhydrous magnesium sulfate and concentrated to yield 5.29 g (97%) of 2-t-butyl-1-indanone. H-NMR (CDCL3) δ 0.95 (s, 9H), 2.38 (dd, J=4.3, 8.0 Hz, 1 H), 2.90 (dd, J=4.3, 17.4 Hz, 1H), 3.08 (dd, J=8.0, 17.4 Hz, 1H) 7.23 (br t, J=7.4 Hz, 1H), 7.35 (br d, J=7.6 Hz, 1H), 7.46 (br t, J=7.6 Hz, 1H), 7.61 (br d, J=7.4 Hz, 1H):

후처리

  1. customDiethyl ether was removed in vacuo
  2. additionTetrahydrofuran (65 mL) was then introduced
  3. customat ambient temperature
  4. customovernight (16 h)
  5. extractionThe solution was extracted with diethyl ether (5*80 mL)
  6. washwashed with water (20 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fee512d3658149189593c90dcc71fcd6
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391991B1

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