Hydrochloric Acid → 1-Cyano-6-methoxy-2-(2-oxo-3-phenylpropyl)-1,2,3,4-tetrahydronaphthalene

HRID 6399

反応式

HRID 6399 の反応式
[O:1]=[C:2]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]([CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]1[C:20]#[N:21])C(OC)=O.[OH-].[Li+].Cl>CO>[C:20]([CH:9]1[C:10]2[C:15](=[CH:14][C:13]([O:18][CH3:19])=[CH:12][CH:11]=2)[CH2:16][CH2:17][CH:8]1[CH2:3][C:2](=[O:1])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)#[N:21]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 19793281Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate

生成物 1

HCID 197932351-Cyano-6-methoxy-2-(2-oxo-3-phenylpropyl)-1,2,3,4-tetrahydronaphthalene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate (4.63 g, 12 mmol), from Step 1, was dissolved in 100 mL of methanol and lithium hydroxide (77 mL of a 1.0M solution) was added. The reaction mixture was stirred overnight at ambient temperature and then acidified with 1N aqueous hydrochloric acid solution and extracted with diethyl ether. The ether extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The basic ether extract yielded 2.76 (70% yield) of the title compound; MS DCl--NH3M/Z: 337 (M+H)+.

後処理

  1. extractionextracted with diethyl ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. extractionThe basic ether extract

出典と根拠

ORDレコード
ord-b7636b58c9434354a2f9df4dde371baa
出典データセット
uspto-grants-1993_09
特許番号
US05248677

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