Lithium hydroxide, monohydrate → (2-Bromo-4-(4-ethoxybenzyl)phenyl)methanol

HRID 1716950노트

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HRID 1716950 반응식
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:8][C:7]=1[Br:22])(=O)C.O[Li].O>C1COCC1.CO.O>[Br:22][C:7]1[CH:8]=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)[CH:10]=[CH:11][C:6]=1[CH2:5][OH:4]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 590134702-Bromo-4-(4-ethoxybenzyl)benzyl acetate

생성물 1

HCID 59013454(2-Bromo-4-(4-ethoxybenzyl)phenyl)methanol수율 92.3%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
25 °C

실험 절차

To a solution of 2-bromo-4-(4-ethoxybenzyl)benzyl acetate (0.215 g, 0.59 mmol) in 10 mL of THF/MeOH/H2O (2:3:1) was added LiOH.H2O (0.051 g, 1.21 mmol). After the reaction mixture was stirred at 25° C. for 3 hours, the volatiles were removed using a rotary evaporator. The residue was dissolved in EtOAc, washed once with brine and dried over Na2SO4. The volatiles were removed using a rotary evaporator to yield 0.175 g of the title compound, which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.38-7.36 (m, 2H), 7.13 (d, J=7.6 Hz, 1H), 7.07 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 4.71 (s, 2H), 4.01 (q, J=7.2 Hz, 2H), 3.88 (s, 2H), 1.92 (bs, 1H), 1.40 (t, J=7.2 Hz, 3H); MS ESI (m/z) 320 [M+], calc. 320.

후처리

  1. customthe volatiles were removed
  2. customa rotary evaporator
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed once with brine
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed
  7. customa rotary evaporator

출처 및 근거

ORD 기록
ord-664dcd452c2b4359b0481638621156dc
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803778B2

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