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Lithium borohydride → (2RS,3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediol

HRID 1956067
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HRID 1956067 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][CH:6]([CH:14]([OH:16])[CH3:15])[C:7](OC(C)(C)C)=[O:8].[BH4-].[Li+]>C(OCC)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][CH:6]([CH:14]([OH:16])[CH3:15])[CH2:7][OH:8]
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참가 물질

5

반응물 2

HCID 4148881Lithium borohydrideHCID 53695590tert-butyl (2RS,3RS)-2-(3,4-dichlorobenzyl)-3-hydroxybutanoate

생성물 1

HCID 19073701(2RS,3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediol수율 90%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

실험 절차

3.0 g of the alcohol compound thus obtained was dissolved in a liquid mixture of 30 ml of ethyl ether and 30 ml of tetrahydrofuran, and 1.2 g of lithium borohydride was added thereto with stirring under cooling with ice. The mixture was stirred at room temperature for 3 hours. The reaction solution was diluted with ethyl ether, then washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 2.1 g (yield: 90%) of (2RS,3RS)-2-(3,4-dichlorobenzyl)-1,3-butanediol.

후처리

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringThe mixture was stirred at room temperature for 3 hours
  4. washwashed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was separated by filtration
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-9a9846dcc47944b7a43b901c910e775d
출처 데이터셋
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05777150

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