Sodium Iodide → 4-(Iodomethyl)-1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octane

HRID 1855083노트

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HRID 1855083 반응식
CC1C=CC(S(O[CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:22]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=O)=O)=CC=1.[Na+].[I-:35]>CC#N>[I:35][CH2:12][C:13]12[CH2:20][CH2:19][C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:22]=3)([CH2:17][CH2:18]1)[O:15][CH2:14]2

참가 물질

4

반응물 2

HCID 5238Sodium IodideHCID 90408232(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

생성물 1

HCID 904081314-(Iodomethyl)-1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octane수율 87%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

A mixture of (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate (1G; 950 mg, 2.05 mmol) and NaI (3.07 g, 20.45 mmol) in MeCN (10 mL) was heated to 70° C. for 72 h. The reaction mixture was cooled to rt, filtered and concentrated in vacuo. The residual crude product was purified by flash chromatography to give the title compound (745 mg, 1.77 mmol; 87% yield) as a white solid. LCMS, [M+H]+=421; 1H NMR (400M Hz, CDCl3) δ 7.38-7.23 (m, 3H), 7.19-7.08 (m, 3H), 7.04-6.98 (m, 2H), 6.87 (ddd, J=8.0, 2.3, 1.0 Hz, 1H), 3.88 (s, 2H), 3.07 (s, 2H), 2.18-1.95 (m, 4H), 1.87-1.68 (m, 4H).

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residual crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-f73413eaf3b549e7ace0b011a5d0498f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962660B2

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