Triethylamine → HCID 20238794, compound

HRID 365049Notes

Reaction equation

HRID 365049 reaction equation
Cl.[CH3:2][NH:3][OH:4].C(N(CC)CC)C.[CH2:12]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)[CH2:13][CH2:14][CH2:15][CH3:16]>C1COCC1.O.CCOC(C)=O>[OH:4][N:3]([CH3:2])[C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:17]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 1708124-Pentylbenzoyl chloride

Product 1

HCID 20238794HCID 20238794, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of N-methylhydroxylamine hydrochloride (793 mg, 2 eq.) in 20 ml of THF:H2O (1:1) with triethylamine (198 ml, 3.0 eq.) was added 4-(n-pentyl) benzoic acid chloride (1.0 ml, 4.75 mmol). The solution was stirred for 0.5 hour at 0° C. then allowed to warm to room temperature and stir overnight. The reaction mixture was diluted with EtOAc and the organic layer was washed with H2O, 1N HCl (2×), and brine, then dried over anhydrous MgSO4. Concentration in vacuo gave a yellow oil which was flash chromatographed in LPS-1 silica gel eluting with (1:1) hexane/EtOAc. Product containing fractions were concentrated in vacuo to yield title product, 380 mg (37%) as a light yellow oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir overnight
  3. washthe organic layer was washed with H2O, 1N HCl (2×), and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentration in vacuo
  6. customgave a yellow oil which
  7. customchromatographed in LPS-1 silica gel eluting with (1:1) hexane/EtOAc
  8. additionProduct containing fractions
  9. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-ad5f938e7db94616922066c5222f8825
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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