Water → HCID 57828250, compound

HRID 2036269Notes

Reaction equation

HRID 2036269 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1.[C:14]([NH:21][CH2:22][CH2:23][CH2:24]Br)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:17]([O:16][C:14](=[O:15])[NH:21][CH2:22][CH2:23][CH2:24][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4][CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 3442904-Hydroxy-1-naphthaldehydeHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 57828250HCID 57828250, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-naphthalene-1-carbaldehyde (15.2 g, 58.1 mmol) in DMF (50 mL) at r.t. was added N-Boc 3-bromo-propylamine (15.2 g, 63.9 mmol), followed by potassium carbonate (12 g, 87.2 mmol). The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture and extracted by CH2Cl2. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was recrystallized from EtOAc/hexane to afford [3-(4-formyl-naphthalen-1-yloxy)-propyl]carbamic acid tert-butyl ester (13.8 g, 72%) as a light yellow solid.

Workup

  1. extractionextracted by CH2Cl2
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-a15cb50047ae43619a9a868329c027f6
Source dataset
uspto-grants-2013_11
Patent number
US08575176B2

Reaction notes

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