(+-)-2-Butanol → HCID 22014126, compound

HRID 1532881Notes

Reaction equation

HRID 1532881 reaction equation
[CH:1]1([CH2:7][C@H:8]2[CH2:10][O:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][CH:12]([OH:15])[CH2:13][CH3:14]>CN(C=O)C.[H-].[Na+]>[CH:12]([O:15][CH2:10][CH:8]([OH:9])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([CH2:13][CH3:14])[CH3:11]

Participants

5

Reactant 2

HCID 6568(+-)-2-ButanolHCID 59949024HCID 59949024, compound

Product 1

HCID 22014126HCID 22014126, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 24758Sodium hydrideSolvent

Procedure

The product from Example 1308C (420 mg, 3.0 mmol) in DMF (3.0 mL), 2-butanol (1.1 mL, 12.0 mmol) in DMF (6.0 mL) and NaH, 60% dispersion in mineral oil, (240 mg, 6.0 mmol) in DMF (12 mL) were allowed to react in a manner similar to that described in Example 1308D. The residue was chromatographed (silica gel; EtOAc/hexanes, 1:12) to afford a clear oil (355 mg, 55%). MS (CI/NH3) m/z: (M+NH4)+ 232.

Workup

  1. customto react in a manner similar to
  2. customThe residue was chromatographed (silica gel; EtOAc/hexanes, 1:12)

Sources & evidence

ORD record
ord-81070838f216473e8dd8179191204a7d
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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