Ethanol → 4-Benzyloxy-2,2-dihydroxymethylbutanol

HRID 514633ノート

反応式

HRID 514633 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 537962344-Benzyloxy-2,2-dihydroxymethylbutanol収率 69.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-306cb0c3294e4c209de3d65c3499c984
出典データセット
uspto-grants-2015_08
特許番号
US09107964B2

反応ノート

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