Aluminium lithium hydride → (4-(Benzofuran-2-ylmethoxy)phenyl)methanol

HRID 2061381노트

반응식

HRID 2061381 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([C:16](OCC)=[O:17])=[CH:14][CH:13]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 59603176Ethyl 4-(benzofuran-2-ylmethoxy)benzoate

생성물 1

HCID 66601277(4-(Benzofuran-2-ylmethoxy)phenyl)methanol수율 67.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Compound 93 (400 mg, 1.29 mmol) was dissolved in THF (15 mL) and LiAlH4 (49 mg, 1.29 mmol) was added portionwise, with vigorous stirring. The suspension was stirred at room temperature for 1 h. THF was evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO4). EtOAc was evaporated off in-vacuo to obtain (4-(benzofuran-2-ylmethoxy)phenyl)methanol (220 mg, 67%) as a crude product. This was dissolved in toluene (10 mL). The solution was cooled to 0° C. PBr3 (98 μL, 1.04 mmol) was added dropwise over 15 min. The resulting mixture was stirred at room temperature for 1 h. It was then washed with saturated K2CO3 solution and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with brine and dried (MgSO4). The solvent was evaporated off in-vacuo to obtain 2-((4-(bromomethyl)phenoxy)methyl)benzofuran as a colourless oil, (132 mg). This intermediate was used in the following reaction.

후처리

  1. customTHF was evaporated off in-vacuo
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customEtOAc was evaporated off in-vacuo

출처 및 근거

ORD 기록
ord-4117c38ae444458282bea774e4053c7b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283340B2

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