Ethanol → 107756-12-7

HRID 868354Notes

Reaction equation

HRID 868354 reaction equation
[O-]CC.[Na+].[Na].C(O)C.C([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][N:15]=1)(=O)C>C(Cl)(Cl)Cl.O.C(O)(=O)C>[C:23]([O:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[N:15][CH:16]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 545296931,1-Dimethylethyl 6-[(acetyloxy)methyl]-3-pyridinecarboxylate

Product 1

HCID 21287980107756-12-7

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of sodium ethoxide, prepared from 0.5 g of sodium and 12.5 ml of dry ethanol, is added to a solution of the crude 5-t-butoxycarbonyl-2-pyridylmethanol acetate in 26 ml of chloroform, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is neutralized by adding a solution of 3.3 ml of acetic acid in 65 ml of water and extracted with three 70-ml portions of chloroform. The combined extracts are dried over magnesium sulfate and concentrated to give 4.1 g of 5-t-butoxycarbonyl-2-pyridylmethanol.

Workup

  1. extractionextracted with three 70-ml portions of chloroform
  2. dry with materialThe combined extracts are dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e1dc74ab0e7a418bb8e549dd853a70f4
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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