Sodium borohydride → HCID 12044322, compound

HRID 991872Notes

Reaction equation

HRID 991872 reaction equation
O.O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Ce+3].[CH3:12][C:13]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[C:14]=1[CH:20]=[CH:21][C:22]#[C:23][C:24]1[CH:38]=[CH:37][C:27]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])=[CH:26][CH:25]=1.[BH4-].[Na+]>C(O)C>[OH:19][CH:15]1[C:14](/[CH:20]=[CH:21]/[C:22]#[C:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:35])[CH3:36])=[O:29])=[CH:37][CH:38]=2)=[C:13]([CH3:12])[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 57027195HCID 57027195, compound2×

Product 1

HCID 12044322HCID 12044322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Cerium trichloride heptahydrate (4.88 g, 13.1 mmol) and (trimethylsilyl)ethyl 4-(4-(2-methyl-6-oxocyclohexen-1-yl)but-3-en-1-ynyl)benzoate (Compound D, 500 mg, 1.31 mmol) were dissolved in ethanol (80 mL), cooled to 0° C. and treated with sodium borohydride (495 mg, 13.1 mmol) in three equal portions. The resulting solution was stirred in the dark for 20 minutes at 0° C. The excess hydride was quenched by the addition of saturated aqueous NH4Cl and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with water, and brine, dried (MgSO4), filtered and the solvents were removed in vacuo. The residue was purified by silica gel chromatography using a solution of hexane and ethyl acetate in a 5 to 1 ratio, respectively, to give the racemic title compound as a yellow oil.

Workup

  1. customThe excess hydride was quenched by the addition of saturated aqueous NH4Cl
  2. extractionthe mixture was extracted 3 times with ethyl acetate
  3. washThe combined organic layers were washed with water, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b21563c3201b4480934050b10b4dc127
Source dataset
uspto-grants-2002_10
Patent number
US06465647B1

Reaction notes

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