Tetrahydrofuran → HCID 18969768, compound

HRID 399073Notes

Reaction equation

HRID 399073 reaction equation
CO[C:3]1([CH2:24]CCC)[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:34]1COCC1>>[CH3:24][C:3]1([CH3:34])[CH:6]([OH:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]1[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 18969745HCID 18969745, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18969768HCID 18969768, compound

Conditions

Temperature
0 °C

Procedure

To a solution of Example 14 (100 mg) in THF (1 mL) at 0° C., was added LAH (1M, THF, 920 μL). The mixture was stirred at 0° C. for min., quenched with H2O, and diluted with EtOAc. The organic phase was washed with HCl 1N, brine, dried (MgSO4) and the solvents evaporated. The residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30)) to give the title compound as a white solid, m.p. 79°-81° C.

Workup

  1. custom, quenched with H2O
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with HCl 1N, brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated
  6. customThe residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30))

Sources & evidence

ORD record
ord-cb53d749ac4440cf90ed5c416bfc733e
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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