Diisobutylaluminum hydride → HCID 90409612, compound

HRID 1855098Notes

Reaction equation

HRID 1855098 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH:24]=[O:25])([CH2:18][CH2:19]2)[O:16][CH2:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][OH:25])([CH2:18][CH2:19]2)[O:16][CH2:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 90409258HCID 90409258, compound

Product 1

HCID 90409612HCID 90409612, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of 110C compound (35 mg, 0.10 mmol) in DCM (2 mL) was added DIBAL-H (0.16 mL of a 1M solution in toluene; 16 mmol) and the solution was stirred at −78° C. for 2 h. The reaction was quenched with sat′d aq. NaH4Cl and CELITE® (200 mg) was added. The mixture was stirred at rt for 30 min, then was filtered through a 1:1 mixture of CELITE® and MgSO4 and concentrated in vacuo to give the title compound (22 mg, 77% yield). LCMS [M+H]+=339.4.

Workup

  1. customThe reaction was quenched with sat′d aq. NaH4Cl and CELITE® (200 mg)
  2. additionwas added
  3. stirringThe mixture was stirred at rt for 30 min
  4. filtrationwas filtered through a 1:1 mixture of CELITE® and MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-582019b2eb7a4d26827d433e544d9c5a
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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