Diisobutylaluminum hydride → HCID 53822047, compound

HRID 2186526Notes

Reaction equation

HRID 2186526 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:25]2[O:30][C:28](=[O:29])[CH2:27][CH2:26]2)[CH:12]=[C:13]([S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])[C:14]=1[O:15][CH2:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[OH:29][CH:28]1[CH2:27][CH2:26][CH:25]([C:11]2[CH:12]=[C:13]([S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])[C:14]([O:15][CH2:16][CH2:17][CH3:18])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[O:30]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54488645HCID 54488645, compound

Product 1

HCID 53822047HCID 53822047, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of 4-(3-benzyloxy-4-propoxy-5-propylsulfonylphenyl) butyrolactone (6.90 g, 0.015 mol) in dry toluene (65 ml) at −78° C. was added 0.9 M toluene solution of DIBAL-H (3.40 g, 26.61 ml) dropwise at −78° C. and stirred for 1 h. Upon completion, the reaction was quenched by adding methanol (7 ml) at −78° C. The mixture was warmed to −20° C. followed by the addition of saturated sodium potassium tartarate solution while maintaining the temperature between −10° C. and 0° C. The mixture was stirred at 0° C. for 1 h. Then the two phases were separated, the aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with water followed by brine, dried (Na2SO4), filtered and concentrated. The crude 2-hydroxy-5-(3-benzyloxy-4-propoxy-5-propylsulfonylphenyl) tetrahydrofuran (6.86 g) was used for the next step without further purification (99%). TLC: Acetone:benzene (1:9), Rf=0.33; 1H NMR(CDCl3, 200 MHz): δ 1.03 (m, 6H), 1.65-2.15 (m, 7H), 2.3-2.6 (m, 1H), 3.35 (m, 2H ), 4.15 (t, J=6.45 Hz, 2H), 4.98 (apparent t, J=6.97 Hz, 0.5H), 5.18 (t, J=6.51 Hz, 0.5H), 5.15 (2s, 2H), 5.6, 5.75 (brs, 1H), 7.1-7.22 (m, 1H), 7.3-7.48 (m, 6H). FAB Mass: 434 (M+).

Workup

  1. customUpon completion, the reaction was quenched
  2. additionby adding methanol (7 ml) at −78° C
  3. additionfollowed by the addition of saturated sodium potassium tartarate solution
  4. temperaturewhile maintaining the temperature between −10° C. and 0° C
  5. stirringThe mixture was stirred at 0° C. for 1 h
  6. customThen the two phases were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washthe combined organic layer was washed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude 2-hydroxy-5-(3-benzyloxy-4-propoxy-5-propylsulfonylphenyl) tetrahydrofuran (6.86 g) was used for the next step without further purification (99%)

Sources & evidence

ORD record
ord-95c1dc462a4c4676ac8975b0995a9c73
Source dataset
uspto-grants-2002_06
Patent number
US06403814B1

Reaction notes

Loading…