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

HRID 2185888노트

반응식

HRID 2185888 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6d21d6da627c43709fb64a9ce32a8289
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403601B1

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