Aluminium lithium hydride → 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol

HRID 1361913ノート

反応式

HRID 1361913 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:20])[O:12][C@H:11]([CH2:13][CH2:14][C:15](OCC)=[O:16])[CH2:10][O:9]1>O1CCCC1>[CH3:7][C:8]1([CH3:20])[O:12][C@H:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:10][O:9]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 22831642Ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate

生成物 1

HCID 109208123-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of lithium aluminium hydride (1.40 g, 35.6 mmol) in anhydrous tetrahydrofuran (100 mL) was added dropwise a tetrahydrofuran solution (30 mL) of ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate (6.00 g, 29.7 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at room temperature overnight, then quenched with the addition of water (1.4 mL) and 10% aqueous sodium hydroxide (1.4 mL). The white solid was removed by filtration, and the filtrate was concentrated in vacuo. The residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic phase was washed with brine, dried (sodium sulfate), and concentrated in vacuo to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 4.03-4.13 (m, 2H), 3.65-3.69 (m, 2H), 3.50-3.55 (m, 1H), 1.61-1.69 (m, 4H), 1.32 (s, 3H), 1.24 (s, 3H).

後処理

  1. customquenched with the addition of water (1.4 mL) and 10% aqueous sodium hydroxide (1.4 mL)
  2. customThe white solid was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f401e00101b54f679455018b6ffaf53c
出典データセット
uspto-grants-2011_02
特許番号
US07880014B2

反応ノート

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