Acetic Acid → 4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid

HRID 1061293

反応式

HRID 1061293 の反応式
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[OH-].[Na+].C(O)(=O)C>CO>[O:15]1[C:14]2([CH2:19][CH2:20][N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:21])=[O:3])=[CH:6][CH:7]=3)[CH2:12][CH2:13]2)[O:18][CH2:17][CH2:16]1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 12717439Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

生成物 1

HCID 159484254-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid収率 99%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid ethyl ester (14 g, 48.1 mmol) (Taylor, E. C., Skotnicki, J. S. Synthesis, 1981, 606) in methanol/tetrahydronfuran (1:1, 100 mL) and sodium hydroxide (2N, 150 mL) was refluxed for 2 hours. After cooling to room temperature the solution was acidified by acetic acid and the solid which was formed was collected and dried to give the title compound as a white solid (12.5 g, 99%); 1H NMR (300 MHz, CDCl3) δ 1.67 (t, J=5.6 Hz, 4H), 3.43 (t, J=5.6 Hz, 4H), 3.92 (s, 4H), 6.96 (d, J=9.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H); MS (ES) m/z: 264.4 (MH+); HRMS Calcd. for C14H17NO4 (M+): 263.1158. Found: 263.1160.

後処理

  1. temperaturewas refluxed for 2 hours
  2. customthe solid which was formed
  3. customwas collected
  4. customdried

出典と根拠

ORDレコード
ord-7626490ea1d142d7bb12b6a12975f400
出典データセット
uspto-grants-2003_02
特許番号
US06525202B2

関連ノート

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