Tetrahydrofuran → HCID 18954662, compound

HRID 2380568Notes

Reaction equation

HRID 2380568 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:3]1.C[Li].[C:16]1(=O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH2:17]1.[NH4+].[Cl-].[O:29]1CCCC1>>[C:19]1([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:7]=2[C:4]([NH:3][C:2]([CH3:13])([CH3:1])[CH2:6][OH:5])=[O:29])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][CH:18]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 107241-TetraloneHCID 25517Ammonium ChlorideHCID 11789738HCID 11789738, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 18954662HCID 18954662, compoundYield 17.6%

Procedure

Preparation of: ##STR39## To a stirred and cooled (-78° C.) solution of 26.4 g of 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine in 200 ml of tetrahydrofuran (distilled over LiAlH4) there were added 70 ml of methyl lithium under a nitrogen atmosphere. Stirring was continued for 2 hours at 0° C. At -78° C., there was added a solution of 22 g of 3,4-dihydro-1(2H)naphthalenone in 50 ml of tetrahydrofuran. After stirring overnight at room temperature, the reaction mixture was poured into a saturated NH4Cl solution. The product was PG,25 extracted with diethyl ether and the extract was dried, filtered and evaporated. The residue was recrystallized from acetonitrile, yielding 8.5 g (17.6%) of 3-(3,4-dihydro-1-naphthalenyl)-N-(2-hydroxy-1,1-dimethylethyl)-4-pyridinecarboxamide; mp. 156.8° C. (comp. 3.031).

Workup

  1. customPreparation of: ##STR39## To
  2. stirringStirring
  3. stirringAfter stirring overnight at room temperature
  4. extractionPG,25 extracted with diethyl ether
  5. customthe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-108cd52abffa418ca50d9e5cf1747371
Source dataset
uspto-grants-1994_11
Patent number
US05369084

Reaction notes

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