Diisobutylaluminum hydride → 4-hydroxymethyl-N-(2-hydroxyphenyl)-benzamide

HRID 970893ノート

反応式

HRID 970893 の反応式
CO[C:3](=[O:20])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][C:5]=1C1C=CC=CC=1O.CC(C[AlH]C[CH:27]([CH3:29])[CH3:28])C>C1COCC1>[OH:20][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:28]2[CH:27]=[CH:29][CH:6]=[CH:7][C:8]=2[OH:9])=[O:9])=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 68619610(2-Hydroxyphenyl)-terephthalamic acid methyl ester

生成物 1

HCID 226013794-hydroxymethyl-N-(2-hydroxyphenyl)-benzamide収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2-hydroxyphenyl)-terephthalamic acid methyl ester (1.31 g, 4.8 mmol) in THF (50 mL) at −78° C. was added a solution of DIBAL-H (27 mL, 1.0 M in THF). The reaction was allowed to warm to room temperature, stirred for 1 h and quenched with a saturated potassium sodium tartrate solution (15 mL). The biphasic mixture was stirred vigorously for 1 h, the phases separated and the organic layer dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (5% MeOH/CH2Cl2) to give 4-hydroxymethyl-N-(2-hydroxyphenyl)-benzamide (0.58 g, 50%). 1H NMR (CDCl3) δ 1.83 (t, 1H (OH)), 4.82 (d, 2H, J=6.0 Hz), 6.93 (t, 1H, J=7.8 Hz), 7.08 (t, 1H, J=7.8 Hz), 7.19 (d, 2H, J=7.8 Hz), 7.53 (d, 2H, J=6.0 Hz), 7.92 (d, 2H, J=7.8 Hz), 8.07 (br, 1H), 8.62 (s, 1H).

後処理

  1. customquenched with a saturated potassium sodium tartrate solution (15 mL)
  2. stirringThe biphasic mixture was stirred vigorously for 1 h
  3. customthe phases separated
  4. dry with materialthe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel (5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-f6e5c80119d449a2a6d97027fc7a1c19
出典データセット
uspto-grants-2007_12
特許番号
US07312234B2

反応ノート

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