Water → 7-methoxy-1'-pentyl-6,7-dihydrospiro[indeno[5,6-d][1,3]dioxole-5,3'-indol]-2'(1H)-one

HRID 425721노트

반응식

HRID 425721 반응식
[OH:1][CH:2]1[C:27]2[C:19](=[CH:20][C:21]3[O:25][CH2:24][O:23][C:22]=3[CH:26]=2)[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3]1.[H-].[Na+].I[CH3:31].O>C1COCC1>[CH3:31][O:1][CH:2]1[C:27]2[C:19](=[CH:20][C:21]3[O:25][CH2:24][O:23][C:22]=3[CH:26]=2)[C:4]2([C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:5]2=[O:18])[CH2:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59263478HCID 59263478, 화합물

생성물 1

HCID 592635027-methoxy-1'-pentyl-6,7-dihydrospiro[indeno[5,6-d][1,3]dioxole-5,3'-indol]-2'(1H)-one수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 7-hydroxy-1′-pentyl-6,7-dihydrospiro[indeno[5,6-d][1,3]dioxole-5,3′-indol]-2′(1′H)-one (0.05 g, 0.14 mmol) in THF (10.0 mL) was added sodium hydride (0.01 mg, 0.21 mmol) at 0° C. The reaction mixture was stirred for half an hour followed by the addition of iodomethane (0.50 mL). The mixture was stirred at ambient temperature for two hours, then poured into water (100 mL), and extracted with ethyl acetate (100 mL). The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (0.03 g, 57%) as an oil: 1H NMR (300 MHz, CDCl3) δ 7.26-7.18 (m, 1H), 6.98-6.82 (m, 4H), 6.10 (s, 1H), 5.88 (s, 2H), 5.26 t, 1H), 3.88-3.63 (m, 2H), 3.45 (s, 3H), 2.71-2.54 (m, 2H), 1.80-1.65 (m, 2H), 1.45-1.29 (m, 4H), 0.90 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 178.3, 148.9, 148.4, 142.4, 136.8, 136.6, 135.1, 128.1, 123.1, 122.6, 108.5, 105.0, 103.2, 101.5, 82.7, 57.9, 55.6, 43.4, 40.3, 29.1, 27.2, 22.4, 14.0: MS (ES+) m/z 402.4 (M+23).

후처리

  1. stirringThe mixture was stirred at ambient temperature for two hours
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

출처 및 근거

ORD 기록
ord-9e35181b0088446ba70f86674dc97031
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106087B2

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