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

HRID 1716950ノート

反応式

HRID 1716950 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-664dcd452c2b4359b0481638621156dc
出典データセット
uspto-grants-2010_09
特許番号
US07803778B2

反応ノート

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