Water → (1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol

HRID 890067

반응식

HRID 890067 반응식
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]=[O:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C(OCC)(=O)C>O1CCCC1.C([Li])CCC>[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][O:2]2)[OH:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 103271,3-DihydroisobenzofuranHCID 895841-Benzylpiperidine-4-carbaldehyde

생성물 1

HCID 22248465(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol수율 37.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 178418339Butyllithium용매

반응 조건

온도
-70 °C

실험 절차

After dissolving 591 mg of 1,3-dihydroisobenzofuran in 10 ml of tetrahydrofuran, 3.9 ml of n-butyllithium (1.5 M, n-hexane solution) was added thereto at −70° C. under a nitrogen atmosphere, the mixture was stirred for 1 hour, and then a solution of 1 g of 1-benzylpiperidine-4-carboxaldehyde in tetrahydrofuran (5 ml) was added dropwise and the mixture was stirred for 1 hour. Water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain 597 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol.

후처리

  1. additionwas added
  2. stirringthe mixture was stirred for 1 hour
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customPurification

출처 및 근거

ORD 기록
ord-b9a9d7ccb3224e999e73bdc462941551
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995144B2

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