Water → HCID 66705014, 화합물

HRID 424368노트

반응식

HRID 424368 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:3]=1[CH2:4][OH:5].C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl.O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:3]=1[CH2:4][O:5][CH2:21][O:22][CH3:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 534078974-Bromo-3-(hydroxymethyl)benzonitrile

생성물 1

HCID 66705014HCID 66705014, 화합물수율 73.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-bromo-5-cyanobenzyl alcohol (4.59 g, 21.7 mmol) in dichloromethane (80 mL) were added diisopropylethylamine (5.6 mL, 32 mmol) and chloromethyl methyl ether (2.3 mL, 30 mmol) at 0° C., and the reaction mixture was stirred at room temperature overnight. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (6:1 hexane/ethyl acetate) to give 18f (4.08 g, 71%): 1H NMR (300 MHz, CDCl3) δ (ppm) 3.43 (s, 3H), 4.65 (s, 2H), 4.80 (s, 2H), 7.43 (dd, J=8.2, 4.1 Hz, 1H), 7.66 (d, J=8.2 Hz, 1H), 7.82 (d, J=4.1 Hz, 1H).

후처리

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (6:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-ef32e5090ddc4e4b932ad0809413b16d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106031B2

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