Tetrahydrofuran → HCID 14894859, compound

HRID 232076Notes

Reaction equation

HRID 232076 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([O:16][CH3:17])=[C:10]([CH3:18])[C:9]=1[CH:19]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=[O:26].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH3:6][O:7][C:8]1[C:13]([CH3:14])=[C:12]([CH3:15])[C:11]([O:16][CH3:17])=[C:10]([CH3:18])[C:9]=1[CH:19]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14576260HCID 14576260, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14894859HCID 14894859, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred tetrahydrofurane solution (40 ml) of 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-(3-pyridyl)heptanoic acid (3.0, 7.8 mmol) prepared in the Reference Example 11 was added lithium aluminum hydride (450 mg, 11.9 mmol) under ice-cooling. The reaction mixture was allowed to rise to room temperature and stirred for 30 min. After that water was carefully added to the reaction mixture and the product was extracted with ethylacetate. The extract was washed with water, dried, and evaporated in vacuo to yield 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-(3-pyridyl)heptanol (2.3 g, 79.6%) as, an oil, after chromatography of the crude product on silica gel.

Workup

  1. temperaturecooling
  2. customto rise to room temperature
  3. extractionthe product was extracted with ethylacetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-52b2e58fe62c4d279fd95638b3ff5102
Source dataset
uspto-grants-1989_07
Patent number
US04851413

Reaction notes

Loading…