Diisobutylaluminum hydride → HCID 86605034, compound

HRID 2378492Notes

Reaction equation

HRID 2378492 reaction equation
C[O:2][C:3](=O)/[C:4](/[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:38])[CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[CH:5]/[CH2:6][C@H:7]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])/[C:8](/[CH3:16])=[CH:9]/[C:10]1[N:11]=[C:12]([CH3:15])[S:13][CH:14]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[C:21]([Si:18]([CH3:20])([CH3:19])[O:17][C@H:7](/[C:8](/[CH3:16])=[CH:9]/[C:10]1[N:11]=[C:12]([CH3:15])[S:13][CH:14]=1)[CH2:6]/[CH:5]=[C:4](\[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:38])[CH2:29][O:30][Si:31]([C:34]([CH3:35])([CH3:36])[CH3:37])([CH3:32])[CH3:33])/[CH2:3][OH:2])([CH3:22])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86605035HCID 86605035, compound

Product 1

HCID 86605034HCID 86605034, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To 13.9 g (23 mmol) of allylic ester XIII in 500 ml of THF at −78° C. was added over 10 min 47 ml (70 mmol) of DIBALH (1.5 M in toluene). The reaction mixture was successively stirred at −78° C. for 3 h, allowed to warm to 0° C. within 30 min. and further stirred at 0° C. for 30 min. before being quenched by the addition of 50 ml of aqueous 0.1N HCl. The layers were separated and the aqueous layer was washed with TBME (2×50 ml). The combined organic extracts were washed with aqueous saturated NaHCO3 (2×50 ml) and brine (50 ml), dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash-chromatography (SiO2, 5:1 heptane/EtOAc) to afford 10.0 g (76%) of allylic alcohol XIV as a pale yellowish oil. Rf=0.16 (SiO2, 3:1 heptane-AcOEt).

Workup

  1. temperatureto warm to 0° C. within 30 min.
  2. stirringfurther stirred at 0° C. for 30 min.
  3. custombefore being quenched by the addition of 50 ml of aqueous 0.1N HCl
  4. customThe layers were separated
  5. washthe aqueous layer was washed with TBME (2×50 ml)
  6. washThe combined organic extracts were washed with aqueous saturated NaHCO3 (2×50 ml) and brine (50 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash-chromatography (SiO2, 5:1 heptane/EtOAc)

Sources & evidence

ORD record
ord-4160d5c79bd14886b31c754c5c9039ee
Source dataset
uspto-grants-2008_12
Patent number
US07470792B2

Reaction notes

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