Hydrochloric Acid → HCID 71245607, compound

HRID 532129Notes

Reaction equation

HRID 532129 reaction equation
[CH2:1]([C:8]1(O)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>O>[CH:1](=[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[O:11][CH2:10][CH:9]1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71245453HCID 71245453, compound

Product 1

HCID 71245607HCID 71245607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

6.87 g (12.5 mmol) of ethyl 4-benzyl-4-hydroxy-6-methoxychroman-3-ylcarbamate were added to 80 ml of half concentrated aqueous HCl and stirred at 100° C. for 2.5 h. The mixture was cooled to 0° C. and diluted with water. Sodium hydroxide (50% aqueous solution) was carefully added until pH >10. The aqueous phase was extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried over MgSO4 and the solvent was evaporated to give 5.7 g of crude material. The crude material was purified by flash chromatography to yield 3.1 g (9.1 mmol, 73° X)) of the desired product.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionThe aqueous phase was extracted with EtOAc (2×)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated
  6. customto give 5.7 g of crude material
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-2919e07c7d024ae1b3f208e675bda6f3
Source dataset
uspto-grants-2014_10
Patent number
US08853196B2

Reaction notes

Loading…