Hydrochloric Acid → HCID 19021767, compound

HRID 1898744Notes

Reaction equation

HRID 1898744 reaction equation
C([O:4][C:5]1[C:6]([CH3:27])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([C:18](=[O:26])[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:17])[CH2:9][CH2:8]2)(=O)C.C[O-].[Na+].Cl.CCOC(C)=O>CO.O>[CH2:20]([NH:19][C:18]([C:10]1([CH3:17])[CH2:9][CH2:8][C:7]2[C:12](=[C:13]([CH3:16])[C:14]([CH3:15])=[C:5]([OH:4])[C:6]=2[CH3:27])[O:11]1)=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 67262986HCID 67262986, compound

Product 1

HCID 19021767HCID 19021767, compoundYield 108%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Crude 2-(hexylcarbamoyl)-2,5,7,8-tetramethylchroman-6-yl acetate (187 mg, 0.25 mmol) in 1.25 mL MeOH was treated with 33.7 mg (0.625 mmol) NaOMe and let stir overnight. The stirred brown solution then was diluted with water (10 mL), neutralized with 2.5 M HCl (1.5 mL) and 10 mL EtOAc added. The layers were separated and the organics dried over Na2SO4 and concentrated. Flash chromatography yielded 90 mg of N-hexyl-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide.

Workup

  1. additionadded
  2. customThe layers were separated
  3. dry with materialthe organics dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d0f2b85afeb4a8b94c2f0cf4e12cc32
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

Loading…