(2R)-3-Benzyloxymethoxy-2-methyl-propionic acid methyl ester → (2R)-3-Benzyloxymethoxy-2-methyl-propan-1-ol

HRID 493059ノート

反応式

HRID 493059 の反応式
C[O:2][C:3](=O)[C@H:4]([CH3:16])[CH2:5][O:6][CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:9]([O:8][CH2:7][O:6][CH2:5][C@H:4]([CH3:16])[CH2:3][OH:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 10082905(2R)-3-Benzyloxymethoxy-2-methyl-propionic acid methyl esterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 11805955(2R)-3-Benzyloxymethoxy-2-methyl-propan-1-ol収率 66%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ester 2 (0.5 g, 2.1 mmol) in anhydrous THF (4 mL) was added dropwise to a suspension of lithium aluminum hydride (0.16 g, 4.2 mmol) in anhydrous THF (10 mL) at 0° C. The cooling bath was removed, and the reaction was stirred at room temperature overnight, quenched with cold water, and extracted with EtOAc. The solvents were removed in vacuum and the crude oil was purified by silica gel chromatography using hexane/EtOAc (8:2) as an eluent to afford oily diol 3 (0.29 g, 66%).

後処理

  1. customThe cooling bath was removed
  2. customquenched with cold water
  3. extractionextracted with EtOAc
  4. customThe solvents were removed in vacuum
  5. customthe crude oil was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-1f9a45735dff4d48a12b89eb30b2f784
出典データセット
uspto-grants-2009_05
特許番号
US07534777B2

反応ノート

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