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Benzyl Bromide → 1-[3-(Benzyloxy)-2-[(benzyloxy)methyl]-2-(4-bromobenzyl)propyl]-4-(diethoxymethyl)benzene

HRID 566509
노트
인쇄 미리보기

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HRID 566509 반응식
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)([CH2:10][OH:11])[CH2:8][OH:9])=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[H-].[Na+]>CN(C=O)C>[CH2:28]([O:9][CH2:8][C:7]([CH2:10][O:11][CH2:6][C:5]1[CH:26]=[CH:27][CH:2]=[CH:3][CH:4]=1)([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:27][CH:26]=1)[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])=[CH:17][CH:18]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 212657092-(4-Bromobenzyl)-2-[4-(diethoxymethyl)benzyl]-1,3-propanediol

생성물 1

HCID 212656851-[3-(Benzyloxy)-2-[(benzyloxy)methyl]-2-(4-bromobenzyl)propyl]-4-(diethoxymethyl)benzene

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

A mixture of 2-(4-Bromobenzyl)-2-[4-(diethoxymethyl)benzyl]-1,3-propanediol(3 g, crude), benzyl bromide (3 mL), and NaH (1.2 g, 60% in mineral oil) in 30 mL of DMF was stirred for 14 h at 70° C. The mixture was then quenched with 5 mL of MeOH followed by 50 mL of saturated NH4Cl and extracted with 200 mL of 2:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 15:1 hexane EtOAc containing 1% of Et3N to give 2.5 g of the title compound as an oil.

후처리

  1. customThe mixture was then quenched with 5 mL of MeOH
  2. extractionextracted with 200 mL of 2:1 hexane/EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 15:1 hexane EtOAc containing 1% of Et3N

출처 및 근거

ORD 기록
ord-1ee26cce31874b15b18e200ab3ca88e7
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06174874B1

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