Tetrahydrofuran → HCID 18666732, compound

HRID 355580Notes

Reaction equation

HRID 355580 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6]/[CH:7]=[CH:8]/[C@H:9]([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CO>[CH3:19][C@H:9]([CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)/[CH:8]=[CH:7]/[CH2:6][CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10446044HCID 10446044, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18666732HCID 18666732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (-)-(R)-6-methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester, prepared by the procedure described in J. Org. Chem., 59(8), 2253 (1994), (1.0 g, 3.8 mmol) and 7.9 mL of anhydrous THF was added dropwise to a 0° C. suspension of LAH (0.03 g, 7.9 mmol) and 7.9 mL of anhydrous THF. The reaction mixture was stirred for 2 hours at 0° C. and for 1 hour at room temperature. After cooling again to 0° C., 1.2 mL of MeOH was added slowly. The mixture was stirred for 0.25 hours at room temperature, then concentrated in vacuo. Saturated aqueous Rochelle's salt was added, and the mixture was extracted with isopropyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (0.84 g) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 0.095 (d, 3H), 1.21-1.38 (m, 3H), 1.51-1.70 (m, 4H), 2.02-2.15 (m, 3H), 2.58 (t, 2H), 3.65 (q, 2H), 5.23-5.45 (m, 2H), 7.18 (m, 3H), 7.28 (m, 2H). MS (DCl/NH3) m/e 250 (M+NH4)+.

Workup

  1. temperatureAfter cooling again to 0° C.
  2. stirringThe mixture was stirred for 0.25 hours at room temperature
  3. concentrationconcentrated in vacuo
  4. additionSaturated aqueous Rochelle's salt was added
  5. extractionthe mixture was extracted with isopropyl acetate
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa2779c7139d47359cfa962e686bc662
Source dataset
uspto-grants-1998_11
Patent number
US05831115

Reaction notes

Loading…