Ethyl Acetate → 2-(2,3-dihydro-1H-inden-2-yl)ethanol

HRID 1669119ノート

反応式

HRID 1669119 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11](OCC)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O>C1COCC1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[CH2:10][CH2:11][OH:12]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 10104359Ethyl 2-(2,3-dihydro-1H-inden-2-yl)acetateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 103520002-(2,3-dihydro-1H-inden-2-yl)ethanol収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ester 148 (68.8 g, 337 mmol) in dry THF (250 mL) was added to dropwise to a suspension of LiAlH4 (20.0 g, 501 mmol) in dry THF (500 mL) at 0° C. and the resulting mixture was stirred for 1.5 h. EtOAc was added to quench excess LiAlH4 and then aqueous H2SO4 solution (10%, 1 L) was added and the organic fraction separated. The aqueous solution was extracted with EtOAc (3×250 mL), and the combined organic fraction dried and the solvent evaporated to give alcohol 149 (54.5 g, 100%) (lit. Tanaka, et. al., J. Med. Chem. 1994, 37, 2071-2078) as a yellow oil: 1H NMR δ 7.16-7.25 (m, 2H, Harom), 7.09-7.14 (m, 2H, Harom), 3.74 (t, J=6.8 Hz, 2H, CH2O), 3.03-3.10 (m, 2H, CH2), 2.53-2.66 (m, 3H, CH2, CH), 1.82 (q, J=6.8 Hz, 2H, CH2), OH not observed.

後処理

  1. customto quench excess LiAlH4
  2. additionaqueous H2SO4 solution (10%, 1 L) was added
  3. customthe organic fraction separated
  4. extractionThe aqueous solution was extracted with EtOAc (3×250 mL)
  5. customthe combined organic fraction dried
  6. customthe solvent evaporated

出典と根拠

ORDレコード
ord-a514da18a2454dbaad1c405da72c4bef
出典データセット
uspto-grants-2011_08
特許番号
US07989451B2

反応ノート

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