Diisobutylaluminum hydride → HCID 22573039, compound

HRID 23469Notes

Reaction equation

HRID 23469 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([S:10]C(=O)N(C)C)=[C:6]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:5]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:16]([C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[SH:10])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54320771HCID 54320771, compound

Product 1

HCID 22573039HCID 22573039, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.1 g (7.1 mmol) of 3-tert-butyl-4-dimethylcarbamoylsulfanyl-benzoic acid methyl ester (Example W) in toluene (100 mL) was cooled to −78° C. and treated with 42 mL of DIBAL (1.0 M in CH2Cl2; 42 mmol). The reaction mixture was allowed to warm to room temperature overnight. The reaction was quenched cautiously with saturated aqueous citric acid and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. Chromatography of the residue over silica gel, eluting with 3:2 hexane:EtOAc, gave the title compound.

Workup

  1. customThe reaction was quenched cautiously with saturated aqueous citric acid
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washChromatography of the residue over silica gel, eluting with 3:2 hexane

Sources & evidence

ORD record
ord-be50447def4a4d2c919ec183f9fe8d31
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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