3-Hydroxybenzyl alcohol → 3-(2-Quinazolinylmethoxy)benzyl alcohol

HRID 1418865노트

반응식

HRID 1418865 반응식
Cl[CH2:2][C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C([O-])([O-])=O.[K+].[K+].[OH:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][OH:24]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[N:12][C:3]=1[CH2:2][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][OH:24]

참가 물질

6

반응물 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 143023852-(Chloromethyl)quinazoline

생성물 1

HCID 543359633-(2-Quinazolinylmethoxy)benzyl alcohol수율 85.8%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5.00 g (28 mmol) of 2-chloromethylquinazoline in 50 ml of DMF, 4.26 g (31 mmol) of K2CO3 and 903 mg (2.8 mmol) of tetra-n-butylammonium bromide were added. 3-Hydroxybenzyl alcohol (3.48 g, 28 mmol) was added further, followed by stirring at room temperature for 5 days. The reaction mixture was concentrated under reduced pressure, followed by the addition of CHCl3 and water to extract the reaction product into the organic layer. The extract was dried over Na2SO4 and then concentrated under reduced pressure. The residue was recrystallized from a CHCl3 -n-hexane mixed solvent, whereby 6.4 g of the title compound was obtained as pale yellow powder (yield: 93.1%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by the addition of CHCl3 and water
  3. extractionto extract the reaction product into the organic layer
  4. dry with materialThe extract was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from a CHCl3 -n-hexane mixed solvent

출처 및 근거

ORD 기록
ord-35f1e9da5ff94e44b5bd28726894b8ce
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05885987

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