Ethanol → 4-Benzyloxy-2,2-dihydroxymethylbutanol

HRID 514633노트

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HRID 514633 반응식
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:22][OH:23])([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(O)C>CO>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:17][OH:18])([CH2:22][OH:23])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 67779176Diethyl 2-(2-benzyloxyethyl)-2-hydroxymethylmalonate

생성물 1

HCID 537962344-Benzyloxy-2,2-dihydroxymethylbutanol수율 69.7%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
25 °C

실험 절차

1.03 g (3.24 mmol equivalents) of diethyl 2-(2-benzyloxyethyl)-2-hydroxymethylmalonate was dissolved in 10 mL of methanol, and this was added dropwise to 1.69 g (44.6 mmol equivalents) of sodium borohydride over 20 minutes. This was refluxed while heating overnight and then cooled to room temperature (25° C.). Water was added to the reaction liquid, and a reaction was carried out for 30 minutes. The reaction liquid was washed with chloroform, and the aqueous phase was concentrated under vacuum. 100 mL of ethanol was added to the obtained residue, and the mixture was refluxed while heating for 2 hours. Immediately after completion of the reaction, the mixture was subjected to silica gel column chromatography (eluent: ethanol) to give 543 mg of 4-benzyloxy-2,2-dihydroxymethylbutanol as an crude product.

후처리

  1. temperatureThis was refluxed
  2. temperaturewhile heating overnight
  3. customThe reaction liquid
  4. washwas washed with chloroform
  5. concentrationthe aqueous phase was concentrated under vacuum
  6. addition100 mL of ethanol was added to the obtained residue
  7. temperaturethe mixture was refluxed
  8. temperaturewhile heating for 2 hours
  9. customImmediately after completion of the reaction

출처 및 근거

ORD 기록
ord-306cb0c3294e4c209de3d65c3499c984
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107964B2

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