Sodium Hydroxide → 3-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

HRID 2185888ノート

反応式

HRID 2185888 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([O:15]C)=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 22452655Methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

生成物 1

HCID 224526443-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid収率 98.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (0.96 g, 4.46 mmol) in THF (54 mL), water (21 mL) and 1N NaOH (9.4 mL, 9.4 mmol) was stirred overnight at room temperature. The THF was removed in vacuo and the mixture acidified to pH 1with 1N HCl. The resulting precipitate was extracted with EtOAc, dried (MgSO4), filtered and concentrated to give the title compound as a white solid (0.88 g, 98%). 1H NMR (DMSO) δ 13.33 (s, 1H), 7.96 (d, 1H), 7.29 (d, 1H), 3.99 (d, 2H), 2.81 (d, 2H), 1.72 (m, 4H); MS m/z 200.1 (M−H).

後処理

  1. customThe THF was removed in vacuo
  2. extractionThe resulting precipitate was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6d21d6da627c43709fb64a9ce32a8289
出典データセット
uspto-grants-2002_06
特許番号
US06403601B1

反応ノート

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