2,3-dihydro-1H-indene-5-carboxylic acid → (2,3-dihydro-1H-inden-5-yl)methanol

HRID 1847571ノート

反応式

HRID 1847571 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16](O)=[O:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1>[CH2:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][OH:17])=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

参加物

4

反応物 2

HCID 2328412,3-dihydro-1H-indene-5-carboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 330183(2,3-dihydro-1H-inden-5-yl)methanol収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of LAH (72.8 g, 1.92 mol) in THF (2.5 L) at 0° C. was slowly added 2,3-dihydro-1H-indene-5-carboxylic acid (100.0 g, 0.62 mol). The reaction mixture was stirred at 0° C. for 1 h. Then the reaction was quenched with H2O (72 ml) and NaOH (68 ml, 20%). The mixture was filtered and the organic layer was dried over Na2SO4, evaporated in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=10:1) to give the desired product (82.0 g, 90%). 1H NMR (CDCl3, 300 MHz); δ 2.03-2.13 (m, 2H), 2.91 (t, J=7.5 Hz, 4H), 4.64 (s, 2H), 7.13 (d, J=7.5, 1H), 7.18-7.24 (m, 2H).

後処理

  1. customat 0° C.
  2. customThen the reaction was quenched with H2O (72 ml) and NaOH (68 ml, 20%)
  3. filtrationThe mixture was filtered
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customevaporated in vacuo
  6. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-a350abf5f05846c1ae800e25d288aaf0
出典データセット
uspto-grants-2015_02
特許番号
US08952050B2

反応ノート

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