Methanol → HCID 19434066, compound

HRID 1736004Notes

Reaction equation

HRID 1736004 reaction equation
[CH3:1][N:2]1[C:7]([C:8](OCC)=[O:9])=[CH:6][C:5]2[CH:13]=[CH:14][S:15][C:4]=2[S:3]1.CC(C[AlH]CC(C)C)C.CO>C1COCC1>[CH3:1][N:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]2[CH:13]=[CH:14][S:15][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydride2×HCID 19434123HCID 19434123, compound

Product 1

HCID 19434066HCID 19434066, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step B (1.00 g, 3.66 mmol) in anhydrous THF (20 mL) at -70° C. was added DIBAL (1.0M, 7.69 mL, 7.69 mmol). The mixture was warmed to ambient temperature and stirred for 2 h, additional DIBAL (20 mmol) was added and the reaction was stirred for 18 h. Methanol (100 mL) was added and the reaction mixture was evaporated to a residue which was suspended in 2N HCl (50 mL) and extracted with ethyl acetate (2×80 ml). The combined extracts were dried (MgSO4) and evaporated to give a solid which was recrystallized from ethyl acetate/hexane to give the desired product (0.80 g, 95%): mp 128°-130° C.

Workup

  1. stirringthe reaction was stirred for 18 h
  2. customthe reaction mixture was evaporated to a residue which
  3. extractionextracted with ethyl acetate (2×80 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customto give a solid which
  7. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b9dc90bf42584ad2bd7aae9018c504b5
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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