Hydrochloric Acid → HCID 19021767, compound

HRID 2428291Notes

Reaction equation

HRID 2428291 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-2b0f97b346414e2083183fb1d64385e2
Source dataset
uspto-grants-2011_06
Patent number
US07968746B2

Reaction notes

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