Hydrochloric Acid → N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 977859ノート

反応式

HRID 977859 の反応式
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:23][C:22]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:20])([CH3:19])[CH3:18].Cl>O1CCCC1>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:23][C:22]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:20])([CH3:18])[CH3:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 19966227N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamideHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 19966239N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

5.96 ml (5.96 mmol) of a 1.0M hexane solution of diisobutylaluminum hydride were added dropwise, over a period of 10 minutes, to 14 ml of a tetrahydrofuran solution containing 702 mg (1.49 mmol) of N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 17) which had previously been cooled at -78° C. The mixture was stirred for 75 minutes at this temperature and then for 45 minutes at room temperature. At the end of this time, the reaction solution was poured into a mixture of dilute aqueous hydrochloric acid and ice, and was then extracted with diethyl ether. The organic extract was washed with water, and then the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 30 g of silica gel. Elution with a 5:4 by volume mixture of methylene chloride and ethyl acetate afforded 427 mg (yield 67%) of the title compound as crystals, melting at 185°-186° C. (after recrystallization from a mixture of methylene chloride and diethyl ether).

後処理

  1. waitfor 45 minutes at room temperature
  2. extractionwas then extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water
  5. customthe solvent was removed by distillation under reduced pressure
  6. washElution with a 5:4
  7. additionby volume mixture of methylene chloride and ethyl acetate

出典と根拠

ORDレコード
ord-9b59a3f001b94cc48b2285be28a19e9b
出典データセット
uspto-grants-1997_03
特許番号
US05614550

反応ノート

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