Methanol → HCID 118108756, compound

HRID 716166Notes

Reaction equation

HRID 716166 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[CH2:18]([N:25]([CH:35]1[CH2:39][CH2:38][O:37][C:36]1=[O:40])[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30](C)=[CH:29][CH:28]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:18]([N:25]([CH:35]1[CH2:39][CH2:38][O:37][CH:36]1[OH:40])[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 86583787Diisobutylaluminumhydride toluene2×HCID 89975793HCID 89975793, compound

Product 1

HCID 118108756HCID 118108756, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

4.4 mL of a 1.5 mol/L diisobutylaluminum hydride/toluene solution was added dropwise to a solution of 2.0 g of N-benzyl-4-methyl-N-(2-oxooxolan-3-yl)benzamide in 30 mL of toluene and 10 mL of methylene chloride at −60° C., and the obtained mixture was then stirred for 30 minutes. Thereafter, the reaction mixture was heated to 15° C., and 6.6 mL of a 1.5 mol/L diisobutylaluminum hydride/toluene solution was added dropwise to the mixture at −60° C. The obtained mixture was stirred for 25 minutes. Thereafter, 1 mL of methanol was added to the reaction mixture, and 80 mL of a 20% potassium sodium tartrate aqueous solution was then added thereto at room temperature. The water layer was removed, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=−60/40 to 35/65), so as to obtain 0.89 g of N-benzyl-N-(2-hydroxyoxolan-3-yl)benzamide in the form of a colorless oily product.

Workup

  1. stirringThe obtained mixture was stirred for 25 minutes
  2. additionwas then added
  3. customat room temperature
  4. customThe water layer was removed
  5. distillationthe solvent was then distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=−60/40 to 35/65)

Sources & evidence

ORD record
ord-2bbbef68b4f64c9faf5d46eac7c0fbdb
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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