Diisobutylaluminum hydride → HCID 44556602, compound

HRID 884375Notes

Reaction equation

HRID 884375 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10][C:9]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:11][CH2:10][CH:9]1[OH:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 57055651HCID 57055651, compound

Product 1

HCID 44556602HCID 44556602, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3.00 g of 136 (6.61 mmol) in 15 ml of anhydrous CH2Cl2 was cooled to −78° C. in an annealed three-necked flask equipped with a dropping funnel and added dropwise with 12.5 ml of DIBAL-H (12.5 mmol, 2.2 eq., 1 M/hexane). After stirring for two hours at −78° C., the reaction was terminated by adding 1 ml of isopropanol, added with 20 ml of K—Na tartrate solution (1.77 M) and slowly thawed to room temperature. After separating the two phases, the aqueous phase was additionally extracted with 3×50 ml of MTBE, and the combined organic phases were dried over MgSO4. After filtration over a short silica gel column (eluted with EE/CH 1:3), the filtrate was concentrated to obtain 204 as a slightly yellowish oil which was further reacted without purification. Yield: 2.92 g (6.41 mmol, 97%).

Workup

  1. customequipped with a dropping funnel
  2. customthe reaction was terminated
  3. additionby adding 1 ml of isopropanol
  4. additionadded with 20 ml of K—Na tartrate solution (1.77 M)
  5. customslowly thawed to room temperature
  6. customAfter separating the two phases
  7. extractionthe aqueous phase was additionally extracted with 3×50 ml of MTBE
  8. dry with materialthe combined organic phases were dried over MgSO4
  9. filtrationAfter filtration
  10. washover a short silica gel column (eluted with EE/CH 1:3)
  11. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5659d074727f4ca3b14148726b7741ff
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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