Diisobutylaluminum hydride → HCID 22988422, compound

HRID 987135Notes

Reaction equation

HRID 987135 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]([CH2:24][CH3:25])[C:20](OC)=[O:21])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][OH:21])=[CH:16][CH:15]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22988432HCID 22988432, compound

Product 1

HCID 22988422HCID 22988422, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl 2-(4-{2-[4-(methylsulfonyl)phenyl]ethoxy}benzyl)butanoate (0:40 g; 1.02 mmole) was dissolved in dry methylene chloride (10 ml) and cooled to −78° C. 1 M DIBAH (3.00 ml; 3.00 mmole) was slowly added and the reaction was stirred over night and allowed to reach r.t. The reaction was cooled to −10° C. and quenched with hydrochloric acid (2 M, 5 ml) and extracted with methylene chloride. The organic phase was dried with magnesium sulfate. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 nmm) using acetronitrile (50%) in ammonium acetate buffer (pH 7) as mobil phase gave 0.24 g (63% yield) of the desired product.

Workup

  1. customto reach r.t
  2. temperatureThe reaction was cooled to −10° C.
  3. customquenched with hydrochloric acid (2 M, 5 ml)
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customPurification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 nmm)

Sources & evidence

ORD record
ord-6bf8534fc85146349f0c03b61e3037bb
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

Loading…