Diethyl Ether → HCID 19739547, compound

HRID 2255032Notes

Reaction equation

HRID 2255032 reaction equation
[CH3:1][C:2]([CH3:32])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:19][CH:18]=1)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Li+].[OH-].[NH4+].[Cl-].CCOCC>CO>[CH3:32][C:2]([CH3:1])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:19][CH:18]=1)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 19739563HCID 19739563, compound

Product 1

HCID 19739547HCID 19739547, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (55) (442 mg, 1 mmol) in MeOH (20 mL), was added LiOH (10 equiv). The resulting mixture was refluxed for 12 hours and then allowed to cool to 25° C. The reaction mixture was poured into a saturated solution of NH4Cl (50 mL) and Et2O (70 mL). The organic layer was separated, dried (MgSO4) and concentrated by rotary evaporation to yield 17) (349 mg, 90%) as a yellow oil; 1H NMR (CDCl3) δ 9.00 (s, 1 H), 7.30 (d, J=7.8 Hz, 2H), 7.18 (d, J=7.8 Hz, 2 H), 4.60 (s, 2 H), 2.94 (t, J=7.8 Hz, 2 H), 2.66 (t, J=7.5 Hz, 2 H), 2.23 (t, J=6.9 Hz, 2 H), 1.52 (s, 6 H), 1.28 (m, 16 H), 0.89 (t, J=6.9 Hz, 3 H); 13 ; C NMR (CDCl3) δ 179.25, 139.24, 137.31, 128.17, 128.08, 84.85, 82.37, 70.79, 6.06, 35.89, 31.89, 30.36, 29.55, 29.32, 29.24, 29.11, 28.82, 28.78, 22.68, 18.60, 14.13. ##STR31##

Workup

  1. temperatureThe resulting mixture was refluxed for 12 hours
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-f472b1f2e1024738b6c6a90b3ad2ca05
Source dataset
uspto-grants-1993_08
Patent number
US05238832

Reaction notes

Loading…