Ammonium Chloride → HCID 67958375, compound

HRID 527546Notes

Reaction equation

HRID 527546 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Cl-].[NH4+]>O1CCCC1.O.[Zn]>[CH3:1][C:2]1([CH3:21])[C:6]2[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67958644HCID 67958644, compound2×

Product 1

HCID 67958375HCID 67958375, compoundYield 77.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3,3-dimethyl-4-[(4-nitrophenyl)oxy]-2,3-dihydro-1-benzofuran (Intermediate 54, 0.9 g) in tetrahydrofuran (20 ml, SCRC) and water (10 ml) were added ammonium chloride (1.687 g, 31.5 mmol, SCRC) and zinc powder (1.031 g, 15.77 mmol, SCRC). The mixture was heated at 40° C. for 2 hours and then filtered through a pad of celite. The filtrate was partitioned with water (20 ml) and ethyl acetate (50 ml, SCRC). The organic layer was dried, evaporated and purified by column chromatography on silica gel (EtOAc/PE=from 1/50 to 1/30) to afford the title compound as a yellow liquid (0.625 g, 76%).

Workup

  1. filtrationfiltered through a pad of celite
  2. customThe filtrate was partitioned with water (20 ml) and ethyl acetate (50 ml, SCRC)
  3. customThe organic layer was dried
  4. customevaporated
  5. custompurified by column chromatography on silica gel (EtOAc/PE=from 1/50 to 1/30)

Sources & evidence

ORD record
ord-e2001bf3b21b4661bdc1f7ac378c4770
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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