Ammonia → HCID 13420661, compound

HRID 615459Notes

Reaction equation

HRID 615459 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][CH2:14][OH:15])[CH2:8][CH2:7][CH2:6]2.N.[Li].CO>O1CCCC1.C(O)(C)(C)C>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][CH2:14][OH:15])[C:10]=2[CH2:11][CH:12]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 3028194LithiumHCID 13420660HCID 13420660, compound

Product 1

HCID 13420661HCID 13420661, compoundYield 126%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1 g (4.8 mmole) of the alcohol product from Example 3 in 15 ml of tetrahydrofuran and 15 ml of t-butyl alcohol was cooled to less than 0°, and 45 ml of distilled liquid ammonia was added. This was followed by the addition over a ten-minute period of 600 mg (86 mmole) of lithium. After three hours, methanol was added to the reaction mixture until the blue color disappeared, and the ammonia was then evaporated under a stream of nitrogen. The residue was dissolved in 5 ml of water, extracted with diethyl ether and acidified with 5% hydrochloric acid. The organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated to dryness. The residue was chromatographed on silica gel to give 1.26 g of the title compound, contaminated with t-butanol. Structure assignment was confirmed by the proton nmr spectrum.

Workup

  1. customthe ammonia was then evaporated under a stream of nitrogen
  2. dissolutionThe residue was dissolved in 5 ml of water
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c6397a43e7be428d803fe720f2acf9cc
Source dataset
uspto-grants-1985_02
Patent number
US04499289

Reaction notes

Loading…