Diisobutylaluminum hydride → HCID 85877534, compound

HRID 1727266Notes

Reaction equation

HRID 1727266 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C(Cl)Cl>[C:14]1([S:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)(=[O:12])=[O:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 364981Methyl 4-((phenylsulfonyl)methyl)benzoate

Product 1

HCID 85877534HCID 85877534, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (2.3 g, 7.92 mmol) from the process (10-2) in CH2Cl2 (50 mL) at −78° C. was added slowly DIBAL-H (1 M in toluene, 16.6 mL, 16.63 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled to 0° C., and to it an aqueous NH4Cl solution (250 mL) was added slowly. The mixture was extracted with 10% MeOH in CH2Cl2 (1.5 L), and the organic layer was dried (MgSO4) and evaporated under reduced pressure. The crude product was crystallized from MeOH/CH2Cl2/ether to afford the titled compound (1.66 g, 80%) as white solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with 10% MeOH in CH2Cl2 (1.5 L)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe crude product was crystallized from MeOH/CH2Cl2/ether

Sources & evidence

ORD record
ord-cd2cfb075ccf43c4ad1ff645e8afc732
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

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