Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate → Benzenemethanol, 4-bromo-3-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 1685658

반응식

HRID 1685658 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][C:9]=1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1>CCOCC>[Br:7][C:8]1[CH:17]=[CH:16][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

참가 물질

4

반응물 2

HCID 16747841Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 16749225Benzenemethanol, 4-bromo-3-[(tetrahydro-2H-pyran-2-yl)oxy]-수율 88.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a suspension of LiAlH4 (0.72 g, 19.04 mmol) in anhydrous Et2O (90 mL) was slowly added a solution of methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate (4.0 g, 12.69 mmol) in anhydrous Et2O (10 mL). The mixture was stirred at room temperature for 2 h and then cautiously quenched with Na2SO4.10H2O (until gas evolution ceases). The solids were filtered off and washed with Et2O (100 mL). The combined organic fractions were then dried (Na2SO4) and concentrated in vacuo. The pale yellow residue was purified by flash column chromatography [SiO2, Et2O/n-hexane (7:3)] to give 4-bromo-3-(tetrahydropyran-2-yloxy)benzyl alcohol as a colourless oil (3.21 g, 88%). δH (270 MHz, CDCl3) 1.54-1.76 (m, 3H), 1.82-2.12 (m, 3H), 3.54-3.64 (m, 1H), 3.8-3.94 (m, 1H), 4.61 (d, J=4.9, 2H), 5.52 (m, 1H), 6.85 (dd, J=7.9, 1.5, 1H), 7.13 (d, J=2.0, 1H), 7.49 (d, J=7.9, 1H), Nb. ArCH2OH too broad to be observed; LC-MS (APCI+): tR=3.84 min, m/z 306.11 (C12H1581BrO4+H3O+), 304.13 (C12H1579BrO4+H3O+); HPLC: tR=2.34 min (96%); HRMS (FAB+) Found 289.02646; C12H16O381Br requires 289.02624.

후처리

  1. customcautiously quenched with Na2SO4.10H2O (until gas evolution ceases)
  2. filtrationThe solids were filtered off
  3. washwashed with Et2O (100 mL)
  4. dry with materialThe combined organic fractions were then dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe pale yellow residue was purified by flash column chromatography [SiO2, Et2O/n-hexane (7:3)]

출처 및 근거

ORD 기록
ord-788ddbbf617f487fae736d0e3d0493b3
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148415B2

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