Chloroacetamide → methyl 9H-fluorene-9-carboxylate

HRID 1607430ノート

反応式

HRID 1607430 の反応式
C1C2C(C(O)=O)C3C(=CC=CC=3)C=2C=CC=1.Cl.CO.[Na].ClCC(N)=O.[CH3:26][O:27][C:28]([C:30]1(O)[C:42]2[CH:41]=[C:40](F)[CH:39]=[CH:38][C:37]=2[C:36]2[C:31]1=[CH:32][C:33](F)=[CH:34][CH:35]=2)=[O:29].[OH-].[Na+]>CO>[CH3:26][O:27][C:28]([CH:30]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=2[C:37]2[C:42]1=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:29]

参加物

8

反応物 6

HCID 6580ChloroacetamideHCID 14798Sodium HydroxideHCID 748099-CarboxyfluoreneHCID 5360545SodiumHCID 14075053Methyl 2,7-difluoro-9-hydroxy-9H-fluorene-9-carboxylateHCID 21893726Hydrochloride methanol

生成物 1

HCID 232396methyl 9H-fluorene-9-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

9H-fluoren-9-carboxylic acid methyl ester (19), which was prepared by refluxing 9H-fluoren-9-carboxylic acid (Aldrich Chemical, Inc.) in HCl/MeOH, (10.0 g, 44.6 mmol) was added to a solution of sodium (1.2 eq, 53.5 mmol, 1.23 g) in 100 mL methanol. After 15 min., 2-chloroacetamide (1.1 eq, 49.1 mmol, 4.59 g) was added and the mixture was allowed to stir at room temperature under nitrogen for two (2) days. The reaction mixture was poured into 400 mL of cold 2.5% w/v aqueous sodium hydroxide and the insoluble material was removed by filtration. The filtrate was chilled and acidified with concentrated hydrochloric acid to precipitate the spiro-succinimide which was collected and air dried to provide 6.7 g (60%). Recrystallization from methanol gave purified (20), 4.28 g (39%). m.p. 237°-239° C. Calc. %C 77.09, %H 4.45, %N 5.62: meas. %C 77.17, %H 4.55, %N 5.58.

後処理

  1. additionThe reaction mixture was poured into 400 mL of cold 2.5%
  2. customthe insoluble material was removed by filtration
  3. temperatureThe filtrate was chilled
  4. customto precipitate the spiro-succinimide which
  5. customwas collected
  6. customair dried
  7. customto provide 6.7 g (60%)
  8. customRecrystallization from methanol
  9. customgave
  10. custompurified (20), 4.28 g (39%)

出典と根拠

ORDレコード
ord-809d66d1256a4b01a8f60228758739be
出典データセット
uspto-grants-1989_09
特許番号
US04864028

反応ノート

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